Bad Before Good
by SouthernBumpkin
Summary: While Serena is away at boarding school, Rufus and Lily begin dating and eventually engaged leading Dan's life to change. Complete Preseries/Season 1 AU.
1. Chapter 1

**A/N: Hey guys, I had to post this again after my brother (He's 12) deleted it, I have no idea what else he did with my profile, but I hope he didn't cause anymore damage (sorry to any authors out there if he had reviewed anything badly). He also deleted my story "Never Look Back," and I don't have it saved on my computer so I'm sorry to the readers who enjoyed that story, but it is forever gone. **

**Anyways, this story starts off a day before Serena comes back from boarding school. During the past year Serena had left the city, Rufus and Lily had been dating, so there was no relationship with Bart Bass and Eric never went to the Ostroff Center.**

* * *

Once Dan's father became engaged to Upper East Side royalty, everything changed.

He didn't know much about Lily, but he remembered Jenny telling him about how much power and influence the Rhode's women had in New York. He thought it was bullshit, but his sister followed these sorts of things so she would know.

He's gotten to know Lily and her family pretty well. Cece doesn't seem to mind him but hates his father. She thinks of him as a gold digger who has been a bad influence on her daughter. Lily had treated him well and their relationship had slowly progressed to motherly status, at least more than his biological mother who is still in Europe discovering herself. His relationship with Eric was strong as well and was probably his only friend at St. Jude's.

Then there was Serena Van Der Woodsen, the blonde he saw dancing on some table at a birthday party. It was disturbing but he was quite infatuated with his future stepsister and tomorrow was the day she would be back from boarding school.

**XOXOXOXOX**

As he watched Lily's penthouse become filled with balloons and a welcome home sign pinned to the wall, he was becoming overwhelmed with anxiety. Today was going to be the first time he would meet Serena.

"You're going to really like her Dan," Eric said patting his back with his hand trying to comfort him. Eric knew about his crush and thought he actually stood a chance.

His eyes found a perfectly put together brunette helping Lily set up.

_Blair Waldorf_

For the past year, their eyes would meet at events and charities he would attend with his father, but they haven't spoken a word to each other. If there was one word to describe Blair, it would be, _bitch_. Jenny looked up to her yet warned him about her which he finds to be quite ironic. She was currently dating Nate who could be considered an Abercrombie Fitch model. People looked at them as the king and queen of the Upper East Side. They were perfect, but he could see right through the bullshit. Nate was clearly distant and Blair seemed unhappy. He was a writer and he could notice little things others couldn't.

The guests started rolling in and he began chowing down the appetizers. It was another party in which he didn't know anyone and felt like an outsider looking in. The women were wearing over the top jewelry and dresses for a welcoming home party. All the guys were in suits while he was wearing a casual button down and vest with jeans looking out of place.

"Hey," Nate said. Dan turned around and found the blue eyed blonde staring at him. "I heard your father recently got engaged to Lily."

"Yeah, last week actually," Dan replied while holding a glass of fruit punch.

"Nate." Nate stuck his hand out and Dan shook it.

"Dan."

"I would've introduced myself earlier if I had any idea you were Rufus's son."

He noticed Nate's eyes trace elsewhere and followed them to find Serena walking into the penthouse. Blair's mom seemed excited to see her while Lily kept her composure. Blair herself was somewhat distant and their hug seemed awkward. His eyes went back to Nate and noticed him slightly uncomfortable to Serena's appearance.

It felt like eternity before Serena reached him. Her skin glistened and her smile lit the room. A part of him was beginning to feel grateful his father was marrying into this family.

"Dan right," Serena inquired knitting her brows together.

"Yeah, it's nice to finally meet you." Dan smiled

"Hey Serena," Nate said

"Natie," Serena yelled excitedly as Nate pulled her in for a hug.

Dan looked over at Blair and found her staring at him. There was clearly something on her mind but he was having trouble reading her. She wasn't even paying attention to Serena and Nate, her eyes were only on him. He was beginning to become tired of this game and was thinking he should just introduce himself, but then he realized he was Dan Humphrey, and she was Blair Waldorf, Queen B of Constance.

He spent the rest of the party getting acquainted with Serena and Nate while Blair was mingling with others. It was very strange to witness, he thought she would want to catch up with her best friend or even spend time with her boyfriend.

**XOXOXOXOX**

Once all the guests had left, he sat with his father and watched him strum his guitar while sitting on the white sofa in the living room of the Van Der Woodsen's.

"I saw you talking to Serena." Rufus smiled and nudged Dan's shoulder playfully. "It looks like you had a good time."

"I did, Serena seems nice," Dan concurred

"I'm happy that you're beginning to make friends with these people, but that doesn't mean you shouldn't be careful. Stick to your morals and don't let them change you," Rufus told him leading Dan to nod.

He heard high heels clicking against the marble floor leading him to glance over and find Serena walking up to them in jeans and a thin long sleeve top.

"I'm going to the Palace, would you like to join me," Serena asked Dan

Dan was hesitant at first because he was uncomfortable going to a place where he didn't think he would be welcomed, but after half an hour of convincing from Serena, he gave in and agreed.

After taking a cab, they reached the lobby of The Palace and entered the elevator. This was his first time in The Palace and he didn't have a clue as to why Eric wasn't joining them. Serena explained that Eric was too young which caused him to become more apprehensive. The elevator stopped and the door slid open. In front of him was a long carpeted hallway with only a few doors. Once they reached their destination, Serena knocked and a smirking Chuck Bass opened the door while holding a drink in his hand.

To put it into simple terms, Chuck Bass was an asshole who only cared about himself, but he was someone you'd want on your side when things got bad. They knew each other pretty well from attending St. Jude's, but said very little words with each other.

"What is he doing here," Chuck sneered looking disgusted.

Before he could turn around and walk away, Serena grabbed his arm. "Well, we are going to be living together so I thought he could get acquainted with my friends, since he is family now," Serena said

Chuck rolled his eyes but slid away to let them in. Chuck's reaction was exactly what he was expecting. People at St Jude's act like Brooklyn was a place filled with paupers trying to squeeze their way into royalty. He's not poor, he's middle class, but that term doesn't exist to these people.

He had to admit the suite was luxurious, the living room itself was larger than his loft. Everything was well furnished and it looked like a professional interior designer worked on the room. As they reached the living room, he saw Blair sitting on the sofa chair with her knees crossed while Nate was rolling a joint on the glass coffee table.

"Why don't you pour yourself a drink," Chuck offered pointing to the bar

"Yeah, I don't even know what to pour," Dan replied

Chuck smiled while Nate looked amused. He glanced over at Blair who was looked as though she was trying to control herself from laughing at him. His cheeks reddened as he nervously rubbed the back of his head. He had never consumed alcohol before and the only thing he knew about was beer and wine. Of course he's heard of scotch and bourbon, but he didn't have a clue as to what it would look like or which one he would actually prefer.

"Why don't I get you some scotch," Chuck said as he walked towards the bar.

"Sure," Dan responded as he sat next to a smiling Nate. He glanced over at Blair who was scanning over his wardrobe and wrinkling her nose to his appearance. "I'm Dan by the way." Dan met her doe eyes

Her heart shaped lips curved slightly. "Blair."

Chuck handed him the drink and sat beside him. "Thanks." Dan raised the drink to Chuck and took a sip. He felt his throat burn which led his eyes to squint leading him to cough.

"Awww, you're so innocent," Serena said while Chuck and Nate chuckled.

"Well it's time to corrupt you Humphrey," Chuck added

"Have you ever smoked," Nate asked

"I've never been offered," Dan said

Nate and Chuck stared at each other and smirked. Nate glanced over to Dan. "Since it's your first time, a joint between me and you won't get you high, it took me my third time smoking to actually get high."

"So what are you saying," Dan asked

"We're just going to have to smoke more than usual," Nate explained while patting him on the back

"I'll get my stash and the bong." Chuck stood up and headed towards the bedroom

His dad told him not to let them change him but here he was, drinking a glass of scotch while waiting to smoke. He always thought he wouldn't let others influence him, but he forgot about something called peer pressure. Peer pressure wasn't something that people forced you to do. It was more of what everyone around you did and you feeling like an outsider because you wouldn't join them.

He's already feeling a bit nervous and guilty, but then he stares over to the blonde goddess and thinks, _Fuck It._

"Blair, you're awfully quiet," Serena questioned with her brows furrowing in confusion. She then looked at Nate then back at Blair. "What's going on?"

"I broke up with Nate," Blair told Serena. Dan could notice her eyes looking very unwelcoming and her jaw clenching. "I'm having difficulty comprehending why you look so surprised."

"This isn't going to be pretty," Nate whispered to Dan

Blair looked over her nails. "Dan, I'm sorry to tell you, but your future step sister is quite a whore," Blair said as Chuck walked in with a bong and his stash.

"You know," Serena stated in a disbelief tone of voice while a smirking Chuck sat beside him

Blair glanced over to Serena with fierce eyes. "That you slept with my boyfriend, yes, it's actually pathetic really, taking the virginity of a boy helplessly in love with you and then running away. You really do exude class."

"I'm so sorry Blair, you know I love you and would never purposely hurt you. It was a mistake. Don't let some drunk night ruin your relationship, it's you he loves," Serena reasoned

Blair laughed bitterly. "I thought that was true once, it was before I overheard my mother talking to Anne Archibald this morning in the kitchen. See to our little Natie, I'm just some business deal."

His jaw dropped hearing the words coming out of her mouth. He knew there was something off about their relationship, but he didn't think it was this bad. Blair Waldorf might have been a cruel manipulative bitch, but he even had sympathy for her at the moment while his view on Serena was slightly changing.

Blair stood up. "Stay the hell away from me," Blair scowled at Serena before walking out of the hotel room.

Serena fell back against the sofa as her face was filled with a mixture of sadness and shock. Nate seemed mortified while Chuck looked amused by the whole scene. It seemed everyone was worried about themselves but no one was thinking to comfort Blair.

"Isn't anyone going to go out there just to check on her," Dan asked

"I think Serena and me are the last people she wants to talk to right now," Nate said. "And Chuck's, well, Chuck."

Dan shook his head and instantly left the room to try and catch up with Blair. Rushing through the hallway, he found her waiting for the elevator with her arms folded across her chest and her foot tapping impatiently against the floor.

"Blair," Dan said as he reached her

Blair rolled her eyes. "What do you want?"

"I just wanted to see if you're okay," Dan said. "Seeing as how it seems you have no one to talk to."

"Yes, well at least it's better than having to talk to you," Blair scoffed

Dan smiled in disbelief and shook his head. "You really make it hard for someone to have any sympathy for you."

"No one is asking for you pity."

She looked unbreakable on the outside, but there was something about her that made him feel like she was actually fragile and breaking down on the inside. There isn't anyone in the world who wouldn't be hurting after being betrayed the way she had.

"Suffering has been stronger than all other teaching, and has taught me to understand what your heart used to be. I have…..," Dan stated.

"been bent and broken, but I hope into a better shape," Blair interrupted softly while meeting his eyes and finishing his quote. "Charles Dickens."

Dan gave her a warm smile. "I'm impressed."

The elevator rung and the door slid open. Blair stepped into the elevator while looking at him curiously. She didn't say a word but never left his eyes as the door slid closed.

He turned his heels and headed back to the room thinking Blair wasn't as horrible as he initially imagined.

* * *

**So what do you think?**


	2. Chapter 2

**A/N: ****I updated a lot faster than I expected and I don't think I can keep this pace up. Anyways, I wanted to give a further explanation for the premise of this story. This fic is going to be about Dan's experience through his junior year of high school after becoming a part of the UES. There will be bits and pieces missing because I am only writing in Dan's POV, but as the story progresses, those questions will be answered. For example, Blair breaking up with Nate was rather abrupt, but I didn't write in Blair's P.O.V. so we don't know how she is truly affected by Nate's actions or all the factors that led to the break up, we only know the main reasons. Once the final chapter is posted, you will get a better understanding of Blair and what happened pre-series.**

**Thank you for the reviews! I really appreciate them.**

**Disclaimer: I don't own the rights to Gossip Girls characters, but it would be nice if I did.**

* * *

When he walked back to Chuck's room, he heard bubbling sounds and glanced over to find Nate taking a hit from a bong. It was as though Blair never stormed out of the room. At least Serena was looking guilty and she had a tinge of sadness in her eyes.

"Humphrey, come on," Chuck called over

Dan sat beside Nate on the couch leading Nate to slide the bong towards him while handing him a lighter. He took a hit and Nate told him to keep the smoke in his throat as long as possible. The longer he kept in his throat, the more he felt like coughing until he finally released the smoke and burst out coughing.

"It's alright man, I was coughing like crazy my first time too," Nate reassured patting his back

It took him a little longer than everyone else, but he started to feel the effects. Being high was unlike anything he had ever experienced. Everything was more amusing, the music playing on the surround sound stereo sounded better, the food tasted better than ever, and he found it impossible to fill his stomach. The best part was that it made everything more humorous.

They filled their time ordering everything on the menu from room service, playing guitar hero, and laughing at the wild stories Chuck told them.

He had to admit, it was fun, but he realized it was time for him to leave once he saw two high-end escorts entering the room in Chuck's arms. Chuck asked him to join in and he found the request to odd, so he left before things got out of hand.

**XOXOXOXO**

His eyes fluttered open to the sunlight hitting his eyes through the window. He looked over to his alarm clock and discovered it was slightly past noon. Staring at his dresser, he reached out for his cellphone and checked for any messages.

_Nate: Want meet up to play soccer at C. Park?_

After a long workout with Nate, they sat on the bench holding water bottles breathing heavily and glistening with sweat.

"You're pretty good," Nate said. "Tryouts are tomorrow, you should come. We're in desperate need of a forward who can set up the striker, in other words me." Nate smirked

"I'll think about it."

Tomorrow was the first day of school and he already had a lot on his plate. He didn't really know his schedule in detail, but, being on the soccer team would look good on his college applications.

There was a brief pause as Dan eyes squinted due to the sunlight. "So, last night was fun," Nate said giving him a wide grin.

"Well, it was a little awkward in the beginning, but overall, it was pretty fun," Dan replied

"Yeah, the whole Blair thing got pretty heated." Nate scratched his head while his eyes were squinting. "The thing is, I know I look like a horrible person, but my whole life, I've felt like everyone has been making decisions for me. Yes, I care about Blair, but I'm kind of happy everything is out in the open because I feel free," Nate explained

"You mean you're free to go after Serena," Dan concluded

"Yes and no, I want Serena, but she would never hurt Blair more than she already has." Nate glanced over at Dan. "All I've ever known is Blair, I want to see what else is out there, who knows, maybe I'll be wrong and Blair turns out to be the one for me, but right now, I can't say that."

Dan knew what Nate was trying to say and in the end, he liked Nate. Yes, Nate was careless at times when it came to Blair, but there was something about him that made him different from all the other guys at St. Jude's. Nate wasn't a snob, he was laid back and just wanted to enjoy life, which reminded him of Serena.

**XOXOXOXO**

His alarm clock buzzed causing his eyes to open in the early morning. He always hated the first day of school. He would never be able to get enough hours of sleep because he would normally be waking up at noon during the summer.

Sliding off the bed to transition into his new morning routine, he began to realize that this year might turn out to be different. For the first time in his short lived high school life, he didn't feel like he was as much of an outsider, and it was because of Serena Van Der Woodsen.

After slipping into his beige slacks and white dress shirt with a red tie wrapped around his collar, he stepped into the kitchen and poured himself some cereal while sitting next Jenny.

"Excited," Rufus asked while smiling

"Very," Dan replied wryly

"Anything new," Rufus inquired pouring himself some orange juice

"I'm going to try out for the soccer team after school," Dan said. A wave of silence passed through as Jenny's jaw dropped. "What?" Dan looked back and forth between Jenny and Rufus looking surprised.

"No offense, but you're supposed to be more of the loner type," Jenny explained

Dan rolled his eyes. "Just because I don't spend my whole day sucking up to Blair Waldorf doesn't mean I'm anti-social."

He recalled painfully watching his sister trying to mingle with Blair at all the social events they would attend only to be shot down and be treated her like complete shit. He never understood why the girls at Constance didn't have any pride.

"I'm not sucking up to her, it's called paying my dues," Jenny scoffed before taking a bite out of her toasted bread. "Have you looked at Gossip Girl lately?"

Dan shook his head. "No."

"You're on it now so you might want to download the Gossip Girl app onto your phone," Jenny said while trying to suppress her laughter.

Dan narrowed his eyes at Jenny. "What?"

"Your alias is Lonely Boy."

Dan sighed and continued on with his breakfast feeling slightly annoyed. After finishing his cereal, he made sure to pack gym shorts and cleats for tryouts, and then left the loft to catch the public bus to school.

Arriving at the courtyard 30 minutes before class, he found it to be packed with students mingling with their social circles. He tossed his things on the wooden table and reached into his messenger bag to pull out _The Brothers Karamazov_. Reading the novel alone, his eyes skid above the book to catch Blair staring at him leading her eyes instantly fall back to her minions. His eyes slowly trailed off to her legs and he had to admit she had great legs. They weren't long, but they were well toned. Sometimes he wondered if the headmaster of the school realized that the girl's school uniforms were a turn on for boys. His eyes went back to her face and he found her staring at him cocking an eyebrow leading a hint of blush to creep up on his cheeks. He instantly went back to his book trying to pretend that he didn't just get caught checking Blair Waldorf out.

"How's it going Lonely Boy," Serena asked with a smile that could melt millions as she sat beside him.

Dan closed the book and glanced over with a smile. "Not bad. You?"

Serena sighed. "It could be going better."

"In other words Blair's still pissed," Dan replied

He followed Serena's eyes to find Blair surrounded by minions with Jenny hovering outside the circle. He never understood the minion thing. People were so desperate to be accepted that they didn't mind being degraded. Sometimes he wished he was attending a public school where they would actually consider this environment strange.

Serena nodded. "Unfortunately." Serena's eyes fell back to Dan. "Do you think I'm a bad person?"

"Well, I think everyone makes mistakes, the difference between a good person and a bad person is actually feeling guilty for their actions."

Serena smiled causing his heart to flutter.

"Danny boy," Nate said as he towered over him and Serena. "Are you excited for tryouts?"

"Can't wait," Dan replied

"Me and Chuck are going to the park for a smoke. You in?"

"No thanks, smoking before school really isn't my thing," Dan said

Nate smiled. "That's cool, I respect that, I'll see you at lunch then." Nate then walked away and left the courtyard.

"Nate seems to be quite fond of you. I think he's been looking for a genuine friend. With Chuck, he didn't really have a choice, they just grew up together, but you seem to be his first real friend," Serena said

In other words, Chuck Bass had his flaws and Nate would have to overlook them because they had been through so much together. His friendship with Nate was genuine, they liked soccer and had the same morals which Nate couldn't say for Chuck.

After chatting with Serena, he left to organize his things in his locker and then left for class.

**XOXOXOXO**

Sitting in class and listening to the teacher go over the syllabus, he looked over and found Blair listening to the teacher intently. First day of classes were always a breeze, the teachers just goes over the course and tries to get to know the students better. He thinks this was going to be his favorite class because Nate and Serena were in it as well, besides, English was his best subject.

As he scanned over Blair's attire, from her perfect little bow tie, to her perfectly curled locks, he started writing about her in his notebook while the teacher continued on with his lecture. He got lost in his thoughts and didn't realize that half an hour had passed.

"Mr. Humphrey," Mr. Lannister called. Dan's eyes left the notebook up to the professor. "What could you possibly be writing, I've been only discussing the course and everything is on the handouts?"

His eyes widened as Mr. Lannister stepped closer to his desk.

"I was just scribbling some things," Dan said

"Well let's have a look shall we," Mr. Lannister replied as he took Dan's notebook and walked back to the front of the class.

Mr. Lannister began reciting his poem to the class.

_When trees in Spring__  
__Are blossoming__  
__My lady wakes__  
__From dreams whose light__  
__Made dark days bright,__  
__For their sweet sakes.__  
__Yet in her eyes__  
__A shadow lies__  
__Of bygone mirth;__  
__And still she seems__  
__To walk in dreams,__  
__And not on earth._

_Some men may hold__  
__That hair of gold__  
__Is lovelier__  
__Than darker sheen:__  
__They have not seen__  
__My lady's hair._

_Her eyes are bright,__  
__Her bosom white__  
__As the sea foam__  
__On sharp rocks sprayed;__  
__Her mouth is made__  
__Of honeycomb._

_And whoso seeks__  
__In her dusk cheeks__  
__May see Love's sign__  
__A blush that glows__  
__Like a red rose__  
__Beneath brown wine._

After the teacher finished reciting his poem, he felt like running away and never looking back. His palms began to sweat as he was hoping no one was able to figure out who he was writing about.

"So you prefer brunettes over blondes Mr. Humphrey," Mr. Lannister teased leading the whole class room to erupt in laughter.

"I…I don't know, I just wrote what I was feeling at the moment," Dan stuttered

"You're very talented, I hope to read more as the semester progresses." Mr. Lannister handed him his notebook and gave him a warm smile.

For the rest of the class, he fought his eyes not to glance over to Blair. He was hoping she didn't come to the realization the poem was inspired by her. He didn't even know why he wrote it. He was just hit by a wave of inspiration and couldn't stop writing.

Once class was over, he packed his things and stuffed it into his messenger bag. As he gathered his things, his eyes glanced over to Blair who was swiftly leaving the room. He felt a sigh of relief not having to be confronted by the malevolent Blair Waldorf.

**XOXOXOXO**

Chewing on his turkey club sandwich, Dan spotted Serena walking up to him looking gloomy. She sat in front of him at his table with a yogurt in her hand.

"Is everything okay," Dan asked

Serena sighed and shook her head. "I don't think Blair will ever forgive me. She just took my invitation to the Kiss on the Lips party and handed it to Jenny."

Dan smirked. "Good for Jenny." Dan noticed Serena frown. "Do you really need an invitation? You're Serena Van Der Woodsen."

Serena perked back up. "You're right. I should still go and show Blair I won't give up easily."

He liked Serena's optimism, but in reality, he imagined it would be difficult for Blair to forgive her. What Serena did was truly awful and would be difficult for anyone to forgive, let alone a vindictive Blair Waldorf. What troubled him more was how easy Nate got off. Nate cheated on Blair and then was only with her because of some business deal between their parents.

He looked over Serena's shoulder and watched Blair strutting towards their table with an envelope in one hand and a yogurt in the other. He couldn't help but think there was something sexy about Blair, maybe it was her wicked personality.

"Well look who it is, the golden girl and her Labrador," Blair said with a mix of fake sweetness coming out of her voice. She glanced over to Dan and handed him an invitation to the Kiss on the Lips party leading his brows to furrow in confusion. "As much as it bugs me to waste such posh paper on someone from Brooklyn, Nate's infatuation with you has forced me to give you this invitation."

Dan doesn't take the invitation and meets Blair's eyes. "I'm going to have to decline since you don't even want me there."

He wasn't going to attend some Blair Waldorf event only to be looked down upon from her for being there. He had too much pride for that.

"You're actually declining the invitation," Blair said in a tone that this was something actually beyond belief.

"Yes, unless you're actually inviting me and it isn't a favor for Nate," Dan replied

Blair rolled her eyes. "Your loss," Blair stated haughtily and turned her heels to head to the other direction.

Dan's eyes fell back to Serena. "I can't believe you were actually friends with her."

Serena giggled. "Dan, you just need to spend more time with her and let her warm up to you."

Once Dan finished his lunch, he went back this locker to gather his books for his next class. When he opened his locker, an invitation the Kiss on the Lips party fell to the floor and it had a handwritten note attached to it.

_Be ready by 8:30 on Friday, Chuck will pick you up in his limo_

Dan smiled and shook his head. As he reached his hand into his locker, he found that the paper with his poem written in Mr. Lannister's class had been torn off from his notebook.

_How the hell did she even open his locker?_

**XOXOXOXO**

It was Friday and Dan didn't have an idea as to what would be deemed appropriate for the Kiss on the Lips party. He had all sorts of suits and tuxes gifted to him by Lily. Dan wasn't the type of person to accept things that he didn't earn, but Lily explained to him about how it would be inappropriate to wear certain clothes to the social events he would have to attend which led him to eventually give him and accept Lily's gifts. Jenny told him to wear a tuxedo with a bow tie so he decided to keep it simple and go with a black Hugo Boss tuxedo.

It was approaching 8:30 and he was feeling nervous. He wasn't typically busy on Friday nights. His weekends would typically consist of watching his dad play at some local bar, going to a social event with his father, or writing short stories. Sometimes he would go to a movie festival by himself, but that only reminded him of Vanessa.

He pleaded with his sister to join him in the limo, but she waved him off claiming it would be unfitting considering she was lucky enough to even be invited to the party. He was beginning to have second thoughts about even going, but it was too late. His phone began ringing and he knew the limo was downstairs.

As he sat in the spacious limo, it was becoming clear as to why girls were willing to let Blair treat them like peasants. Katie and Is actually looked happy instead of the usual miserable demeanor he was used to seeing in school. They were giggling and popping a champagne bottle while the music was blasting, and to his surprise, Blair was giggling along with them. Everyone seemed to be having the time of their life while he sat their shell shocked as to what he was witnessing.

The life of the teenagers from Manhattan's elite was completely different from the average teenager. A normal teenager was typically scheming to get alcohol while spending the whole week trying to find a place to party.

"So what do you think," Chuck asked sitting beside him

"I don't know what to think," Dan replied looking over at Blair and noticing how good she looked in her sparkling silver dress. "Why is everyone so good looking?"

Chuck laughed. "Welcome to the Upper East Side."

He felt Nate's arm wrap around his neck. "Drink up Danny boy," Nate said pulling him closer and handing him a champagne flute filled with champagne.

He took the champagne flute and met Blair's eyes while noticing her lips curl slightly. He was having trouble distinguishing if she was giving him an evil smile or a friendly smile. In the end, he decided not to think too much about it and took a sip of his champagne.

**XOXOXOXO**

They arrived at the party and could hear the music from outside the entrance. Once they entered the party, it looked like they were in a high end night club except the music wasn't too loud as to where they would be unable to speak with one another. The party displayed class, everyone was wearing either a tux or an expensive dress and everything was organized to perfection.

He mingled with a few of his classmates and danced with Gina Phelps, a brunette from his calculus class, but he spent most of his time hanging around Nate and being introduced to other students from St. Jude's.

Eventually, the room fell quiet and he glanced over to the entrance to find Serena walking in a black dress that displayed her curves to perfection. Of course people were surprised with her appearance. The news of her not being invited was all over Gossip Girl and the talk of the school. People were curious as what she did to cause a rift between her and Blair. He wondered what people would think of Serena if they knew the truth.

Soon, all eyes drifted on to Blair as they waited for a response. She didn't seem very pleased and he watched her turn her heels and head towards the staircase leading up to the roof.

Serena walked up to him. "I've caused quite a commotion."

"I'm going to take a guess and say this wasn't your first time," Dan said with a smile

Serena smiled and looked down biting her lip. "Would you like to dance?"

Dan gently took her hand. "Sure."

As they danced on the dance floor with his arm slipped around her waist, he couldn't help but think how easy it was to get lost in her eyes or her smile. There was so much perfection on the outside.

"Dan," Serena called as they swayed

"Yeah."

"Do you think you could check up on Blair," Serena asked looking hopeful

"You can't be serious," Dan replied

"Please, she doesn't have anyone to talk to, and I'm the last person she wants to see right now," Serena said

Dan sighed. "She's not the easiest person to talk to."

"I know, but you're good in these types of situations, and I'm really starting to worry."

Dan nodded and pulled away. He slid through the crowd and reached the door leading to the stairwell. When he opened the door, he saw Blair and Chuck standing beside the first step of the staircase while Chuck had his arms around Blair.

"Get off me," Blair scolded as she pushed Chuck off and slipped away. "It's never going to happen, not even in your dreams Bass." Blair stood firmly with her hand on her hip.

"Really? Because I just dreamt of you last night." Chuck held a smirk.

Blair groaned in repulsion. "Ughhh! You're disgusting."

"Hey," Dan said leading Blair and Chuck to turn around.

Chuck smiled. "Humphrey, why don't you join us?"

Dan leaned against the railing of the staircase. "Sure."

He watched Chuck reach inside his jacket pocket and pull out a bottle of jagermeister. "Want some," Chuck asked

Dan took the bottle from Chuck's hand as he scanned over Blair who seemed to look a bit timid. Taking a sip from the bottle, he began to notice the goose bumps on her bare arms.

Dan slipped his jacket off and handed it to Blair. "Here."

Blair took the jacket and wrapped it around her shoulders. "Thank you," Blair said softly

Before handing the bottle back to Chuck, he took another sip. "So what have you two been up to? Just drinking," Dan inquired

Chuck smirked. "Well the queen needed something to take the edge off, seeing as how Serena is here."

"But you didn't seem to mind her attendance," Blair added

"You should ask her out," Chuck told him

"You just want to watch me get rejected," Dan replied as he watched Chuck take a swig of the bottle.

"That would be quite entertaining to see, but I think you have a shot," Chuck reasoned

Dan tilted his head. "I can't tell if you're trying to help me, or trying to screw me over." Chuck smirked. "You remind me of that cat from Alice in Wonderland." Dan said to Chuck. "You are one sketchy bastard."

He watched Blair bite back a smile and he wondered why she wouldn't just let loose and have fun. It always felt like she didn't want to let anyone in.

"You'll learn soon enough that I'm not the only one," Chuck replied

What Chuck said was true, but he's heard stories of Chuck's darkness and unlike everyone else, Chuck would cross the line.

Chuck tried to pass the bottle to Blair but Dan intruded. "Yeah, I don't think that's a good idea."

"Am I supposed to care for your opinion," Blair questioned.

"Hey, I'm just trying to help you, but if you want to end the night tied up on Chuck's bed, be my guest," Dan retorted.

He watched her step closer while cocking an eyebrow leading him to raise his brows. "My night and shining armor," Blair mocked him while Chuck laughed

Chuck scanned over Blair's body. "Well if I'm not getting any from Blair tonight, I should head back to the party and find someone else who will fulfill my needs," Chuck said and tossed Dan the jagar bottle while heading out of the stairwell.

Dan took a swig from the bottle. "How come you can drink," Blair asked as his eyes squinted once the alcohol reached his throat.

"Because I'm not the one who's upset," Dan replied with a smirk. "Alcohol and anger don't mix well, especially with someone your size, it could get pretty bad tonight."

He noticed her bite her cheeks and watched the frustration reach her eyes. The bottle was lighter than he expected and was only half filled. He thought if they split it, the most they could get was buzzed.

"How about we split it," Dan offered and sat on the bottom of the steps. He then stuck his hand out and watched her take his hand while gracefully sitting down. She looked amazing yet no one had complimented her the whole night. "Just so you know, the hours you spent getting prepared for this party didn't go to total waste."

Blair narrowed her eyes at him and took the bottle from his hand. "My My Daniel, are you flirting with me?"

Dan smiled. "Not quite." Dan then brushed a strand of hair from her eyes and tucked it behind her ear. He then slyly cupped her cheek with the same hand and leaned in while meeting her eyes. "You look really amazing Blair, you have the face and lips of an angel, and you smell like heaven," Dan said softly. He let a brief moment pass between them as their eyes continued to meet. His lips began to curve slightly as he leaned back and slid his hand away from her cheek. "That would be me flirting."

Blair cleared her throat. "Well good thing you weren't," Blair stated haughtily and took a sip from the bottle.

"Of course, the Labrador doesn't stand a chance with the princess."

"I'm sorry, but that's just how society works, not my rules," Blair said

"Well I am going to be living at Lily's soon, so what does that make me then," Dan inquired playfully.

"Hmmm…..A knight," Blair replied and turned to him

"Well that should improve my chances with Serena then," Dan teased

Blair rolled her eyes and took another sip from the bottle. "She already likes you," Blair said handing him the bottle back.

Dan shrugged his shoulders. "Yeah, but I'm sure she'll like the next guy just as much."

Blair arched an eyebrow. "How would you know that? Don't tell me you've been stalking her, although I wouldn't put it past you."

Dan chuckled and shook his head. "Let's just say I'm starting to see her flaws."

"Those rumors are misleading, yes, she's dated around, but none of those guys had treated her right, she just needs a good guy," Blair explained.

He was thrown back by Blair's comment. She was still loyal to a person who committed the ultimate betrayal. It was then he realized Serena and Blair would be fine. Blair just needed time.

"I like her."

"Obviously."

Dan smirked. "But I'm not stupid enough to fall for her." He took another sip of the bottle and passed it back to Blair. He could notice Blair looking thrown off by his admission. "You shouldn't get in the way of Serena and Nate."

"I'm not," Blair responded. Dan raised his brows and looked at her questionably. "I've dated Nate my whole life, how can you expect me to be okay with him dating my best friend."

"Love who you love while you have them. That's all you can do. Let them go when you must. If you know how to love, you'll never run out," Dan stated.

He watched her take his quote in. It was the first time he's had a real genuine conversation with Blair. He's actually never seen her have a normal conversation with anyone. She typically scolds or yells, maybe throw a witty comment here and there.

"I don't know that one," Blair said

Dan began to blush. "It's from Anne Brashares _My Name is Memory_," Dan said quietly while rubbing the back of his head nervously leading Blair to fall apart into laughter. "It was a long summer," Dan defended himself while smiling.

"Did you read sisterhood as well," Blair teased in a fit of giggles leading Dan to roll his eyes. "Humphrey, you're such a girl."

Blair Waldorf was actually laughing. He never thought he would see the day. It's nice and he wouldn't mind seeing more of it. His phone vibrated and a text message appeared across his phone screen.

_Nate: Come outside for a smoke?_

"I have to go, Nate just texted me," Dan said

Blair nodded and handed him back his jacket. "Thank you Dan."

Dan smiled. "Anytime Waldorf."

**XOXOXOXO**

Smoking in an alley wasn't exactly what he pictured when Nate texted him. But here he was standing in a dark alley with Nate and Chuck watching Nate light a joint.

"So what exactly did you and Blair talk about," Nate asked

"Nothing that would deem interest to you….Although I think I convinced her to let Serena date you," Dan said.

He watched Nate's face light up and wide grin begin to form. "Don't mess with me Dan."

Dan smiled. "I'm not, I think she'll be okay with you two dating."

"Congratulations, now can you pass the joint," Chuck said

Nate passed the joint to Chuck and stared at Dan. "You know I love you right?"

Dan chuckled. "I do now."

He didn't know how to feel about Nate and Serena dating. He was practically head over heels for Serena a week ago, but now, he was more confused than ever about his feelings for her. All he knew was Nate was clearly in love with her and that was something he couldn't say.

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**R&R are always welcome**


	3. Chapter 3

**A/N: ****I don't know how I updated this so fast, but here it is. I'm confident the next chapter won't be updated as fast because it is much longer than this one.**

**I wanted to point out that because this is Dan's POV, you didn't get to see Nate and Serena mend things with Blair, or at least try in the last chapter. Again, this story is only in Dan's POV so there will be a lot of things missing because he is not always with all of these characters. There are also going to be minor time jumps after some of the chapters.**

**I'm trying to stay true to the characters and not have them be OOC. So I don't think Nate would be okay with Dan dating Blair because he had been dating her for his whole life at this point in time. I can't say much more because I don't want to spoil the story.**

**Also, I totally agree with the reviewer, I wanted Serena and Dan to be more like brother and sister, but to get to that point, it will take some time because she was Dan's dream girl at one point and there was a definite instant attraction for Serena towards him. **

**Thank you for the reviews, they truly make my day and inspire me.**

* * *

A month had passed since the Kiss on the Lips party and he was beginning to become accustomed to the Upper East Side luxurious lifestyle. Blair and Serena had finally mended their friendship which was great because there was a lot less tension when they would spend time together. Blair was handling Nate and Serena's relationship surprisingly well. Even he had to admit they would go overboard with the PDA, but Blair didn't seem to mind.

"I heard you and Amber have been spending some time together," Eric said as they played Wii tennis at the Van Der Woodsen living room.

"It's not what you think, her sister is attending Dartmouth and she was telling me what she did to get accepted. Losing the usher spot to Nate really destroyed my confidence," Dan explained as beads of sweat were forming on his forehead from the game. "How about you, how's your love life?"

"I broke it off with Asher." A stunned Dan put the game on pause and turned to Eric. "He wasn't ready to come out and I was sick of watching him stick his tongue down some girl's throat."

He was the only person who knew Eric was gay and he would keep the secret to his grave, even though he believed Eric should come out. But Dan also understood that Lily was very narrow minded and might have trouble dealing with it.

"Did you even like him? Or where you with him because he was the only gay kid you knew at St. Jude's," Dan asked. "Because honestly, I never liked that kid."

Eric shrugged his shoulders. "Yeah, I suppose it was more based on convenience than actual love. It's just really difficult to find someone with my circumstances."

Dan received a Gossip Girl alert leading him to look over his phone and discover that Blair had taken Jenny to some night club. He knew Serena and Jenny were going to be with Blair tonight and were supposedly having a girl's night out, but he didn't know they would be taking his sister to a nightclub. He couldn't help but be curious as to why Blair was being nice to his sister. Jenny would tell him about how Blair was slightly less demanding and would invite her to parties freshman never were allowed to attend. She even let Jenny have some of her dresses. It might have had something to do with him, but he wasn't naïve enough to believe that. His father on the other hand had been displeased with Jenny's recent behavior and Dan felt a burden beginning to weigh on him.

"We're going to crash girl's night out," Dan stated

"And Blair won't mind," Eric inquired arching a brow

Dan tilted his head and smirked. "I'm going to go out on a limb and say that she has a soft spot for me."

"Don't even go there Dan. Serena would be pissed if you started dating Blair," Eric said

Dan knitted his brows together. "What are you talking about, she's dating Nate?"

"Serena and Blair can be possessive and immature at times, even if Serena's feelings for you may have dissipated, it doesn't mean she won't be unreasonable about it. You just don't want to get involved with those two because you're literally dealing with children."

"Well, it doesn't matter because I don't have a shot with Blair, and it's not like I like her. I just think she smells nice," Dan told Eric

Eric turned back to the game and un-paused it. "All I hear is denial."

He does not like Blair Waldorf. She stood for everything he was against. She just had nice soft skin and the scent of her perfect hair only caused his spine to tingle.

**XOXOXOX**

After Nate agreed to come with him to the nightclub, they caught a cab together to where the girls had been spotted on Gossip Girl. Once they snuck Eric into the club, they were able to find the girls sitting at a large booth holding their martini's. It was his first time in a night club and it was a little different than he imagined. It was very spacious and wasn't as crowded as a typical night club, but the dance floor itself, was crowded with people.

He spotted Blair sitting in her red jacket with the girls.

"Dan Humphrey, the last person I was expecting to see," Blair said meeting his eyes as a grinning Nate slid next to Serena.

Dan looked over to Jenny and then back to Blair. "Buy me a drink," Dan asked putting his hand out with a smirk. "I heard the Waldorf's were very charitable people." Katie and Is giggled like they knew something which made him curious.

Blair's lips curved slightly as she took his hand and slid off the booth. She led him to the bar with her hand intertwined with his. Once they reached the bar, she let go of his hand and sat on the stool in front of the bar.

"So why is my night out with the girls being rudely interrupted with your presence," Blair asked before she took a sip of her martini.

"You do realize Jenny's only 14," Dan said

"Aww, Cabbage Patch, you actually think I care."

Dan groaned. "Blair, can you please stop calling me that," Dan pleaded

Blair smirked and arched an eyebrow. "Nope."

"Fine have it your way Blair Bear," Dan replied with a satisfying smile leading Blair to groan back.

"How did you know that," Blair asked tersely. "I am going to kill Dorota."

The Van Der Woodsen's had been invited to Dan's loft for dinner one evening and Serena brought Blair along with her. Blair eventually stumbled upon his DVD collection and they began watching movies together which led to him becoming closer to Dorota.

Dan chuckled. "What can I say, she couldn't resist my charm." Blair rolled her eyes. "Can you at least make sure my sister doesn't do something stupid? Like Oh, I don't know, stealing from Waldorf Designs because you dared her to."

He noticed a hint of surprise creep up on Blair's face, but it was swept away immediately and became unreadable once again. Blair leaned into his ear. "Only if you have something to offer," Blair whispered then pulled away with a wicked smile.

"Blair, I am not going to start flirting with Penelope just to get information," Dan told her

"You're no fun," Blair pouted

"Everything is a game to you," Dan stated

"I thought you would've caught on by now," Blair said tilting her head while batting her eyelashes at him.

Blair was an enigma. Sometimes he would see a soft side to her where she would have her guard down, other times, he would have to deal with her dark side. It was frustrating to witness, but he learned most of her actions had valid reasoning behind them.

"You could at least ask me to dance," Blair told him.

Dan smiled and leaned in. "So you can make Serena jealous."

Blair raised her brows. "And the problem with that is…..?"

"You're impossible." Dan smiled while shaking his head as he slid off the stool and offered his hand

She gave him a mischievous smile and took his hand. After tossing her jacket off to her table, they made it to the crowded dance floor where it was impossible for him to hear his thoughts due to the music. He had no idea how to dance. From what Nate told him, he was supposed to let the girl do most of the work.

He watched Blair press her hands against his chest and begin to sway her hips. She then instantly spun around and started grinding her hips against his as her back was pressed against his chest. This was not what he was expecting. He was scolding himself for finding this hot. He couldn't believe how good she was at dancing. His eyes began to close as he could feel the heat of her neck against his nose and cheek.

As his nostrils were becoming consumed with her scent, his hands landed on her slim waist while hers were slowly sliding to her breast, down to her stomach, and in between her thighs. It was clear, she was losing herself to the music. Soon, dancing with Blair was becoming an internal battle. He was thinking of Lily, his mother, and even Jenny, but it wasn't working, he was getting hard. Once he was hard, Blair just started teasing him. She would grind specifically against his hard-on, seemingly enjoying it. She then swiftly spun around and slid her hand up to the back of his head as her hips swayed against his in a deliciously sinful way with her eyes meeting his. He was surprised to find her face flushed and her hair damp. There was a mess of hair sticking to her face and touching the corner of her mouth as she continued to sway to the music while never leaving his eyes. It was pure torture because he was fighting with himself not to brush his lips against hers.

After dancing for what felt like eternity, he leaned his forehead against her as they stepped away from the dance floor. He could hear her breathing irregularly and feel the sweat from the top of her forehead.

"I need to use the restroom," Blair told him softly while feeling her hot breath on his neck.

"Yeah, I'll see you at the table," Dan replied hoarsely

Dan walked back to Blair's table feeling a bit shaken. He slid next to Serena with Nate on her other side.

"Don't tell me I'm losing you to Blair," Nate teased while feigning hurt

Dan chuckled. "Not a chance, you're the best thing to happen to me since donuts," Dan said leading Nate and Serena to laugh.

"I can't believe you're here," Jenny scoffed and rolled her eyes

Dan glanced over to Jenny. "I just wanted to make sure you were okay," Dan said quietly

Jenny raised her brows and folded her arms across her chest. "Really," Jenny inquired looking at him sternly. "Because I just saw my brother practically having sex with Blair Waldorf on the dance floor." Jenny looked down. "And why would you be wearing converses right now?"

"Oh god, you sound exactly like Blair," Dan replied rubbing his head in annoyance

"I'm just giving you fashion advice. I don't need you embarrassing me in front of everyone," Jenny explained

"Says the girl who would eat shit if Blair told you to," Dan retorted

Serena and Nate chuckled. "Okay children, why don't you two play nice. Jenny, your brother is not embarrassing you, and Dan, stop being mean," Serena told them.

It was strange having Serena as his future step sister. She was family and her relationship with Jenny was becoming sisterly, but with him, they felt more like friends with a possible connection. The only thing he knew for sure was that they were going to be living together soon and dating her would've been an awful idea. Especially if things didn't work out, living together would've been awkward if they broke up.

"So you and Blair huh," Serena inquired smirking while wiggling her eyebrows

"Yeah, not happening," Dan replied

"Why not," Serena asked furrowing her brows in confusion

"Because half the time I feel like she finds me repulsive," Dan said leading Serena to laugh. "It's true, I'm not her type and she isn't mine, at least I don't think she is."

Besides, he doesn't know how Nate would feel if he started dating Blair. A part of him feels like Nate wouldn't be okay with it. They were clearly just joking around so he didn't truly know how Nate would respond to it. Nate's been with Blair for his whole life and there should still be some residing feelings left for Blair.

"Who is Eric talking to," Serena asked looking over at the bar.

Dan followed Serena's eyes towards the bar and saw Eric having a conversation with a perfectly groomed preppy boy with blonde hair. The blonde handed him a napkin with a number written on it and he couldn't help but smile while Serena looked curious.

"Why is that guy giving you his number," Serena inquired once Eric reached their table.

"Oh, I've seen him at the tennis courts before. I was interested in playing him sometime, so I asked for his number," Eric explained.

_Very smooth Eric_

For the rest of the night, he spent a majority of his time at the table watching the girls Gossip while Serena and Nate danced. He harmlessly flirted with Katie and Is but they weren't having any of it. If anything, they seemed timid when he would complement them which he found to be odd. It was as though they weren't allowed to speak to him.

Jenny spent the rest of the night drinking and flirting with guys twice her age. He would have to jump in half the time because she was practically throwing herself at them. He doesn't think he had ever seen Jenny this drunk before. It seized to amaze him how different they truly were. Him and Blair didn't drink much and spent the night watching everyone make a fool of themselves.

It was getting late and he knew his father was waiting up on them. Jenny was very drunk and he didn't want his father to think he was anywhere near Jenny. So he left her with Serena and went home deciding she could fend for herself. It was an every man or woman for themself mentally, but he knew Jenny would do the same.

**XOXOXOXO**

His eyes fluttered open to hear screaming coming out of the living room. His father and sister were clearly arguing with each other about last night. He was surprised to hear Jenny have as much energy as she did. He thought she would be too hung-over to argue. Once Jenny yelled out some very harsh things to her father, he heard the front door to the loft slam shut.

He slid off his bed and walked into the living room to find his father rubbing his forehead looking distraught.

"Dad, are you okay," Dan asked sitting on the stool and facing his father who was standing in front of the kitchen counter.

"Did you know she came home at 3 A.M. last night," Rufus told him. "And she was barely conscious." Rufus sighed. "I don't know what is happening with that girl."

"It's probably just a faze," Dan reassured him

"I'm trying to figure out when she started behaving this way and it really just comes down to her spending time with that Blair girl," Rufus said

"Yeah, she did change when she started hanging out with Blair," Dan concurred.

"When Blair came over for dinner that one night, she seemed like such a nice girl."

Dan smiled. "The thing is, Blair's tricky to get a read on, she's kind of this evil, manipulative, guns-blazing, you don't want to mess with type of girl. I mean she will ruin you if you look at her the wrong way."

Rufus knitted his brows together. "And this is the same girl that you've been watching movies with from time to time?"

"Well, she's not that bad," Dan said

Rufus smiled. "I'm having trouble understanding what you mean son."

Dan sighed. "It would probably take me days to explain the complexities and layers of Blair Waldorf, all I can tell you is that Blair isn't the person to blame for Jenny's recent behavior," Dan said. "Comparatively speaking, Blair doesn't drink much at all, she's actually pretty mature when it comes to that stuff."

"I just wish I knew what to do with Jenny."

"Just be there for her," Dan replied

**XOXOXOXO**

After talking to his father, he jumped into the shower and tried to figure out what to do for the rest of his day. Nate was with Serena and he didn't want to be alone with Chuck, so he decided to visit Blair and see if she wanted to watch a movie.

Entering Blair's foyer, he watched Dorota walk in with a warm smile. Out of all the penthouses he had been in, he was most impressed with Blair's. It wasn't the largest, but it was the best designed. It also didn't hurt the fact that she had such a lovable maid.

"Mr. Dan," Dorota greeted

Dan stepped closer and handed Dorota the lilies he had bought. "These are for you, I thought they bring out your eyes."

"Ugh… Can you stop flirting with Dorota," Blair huffed as she walked in from the living room while Dorota giggled like a school girl.

"It's okay to be Jealous Waldorf, I could save my sweet gestures for you," Dan replied with a smirk

Blair folded her arms across her chest and glared at Dan. "Why are you here, I don't recall us having any plans," Blair asked as Dorota left for the kitchen to put the flowers into a vase.

When he met her eyes, he began to notice how puffy they were. It was as though she had been in tears. He stepped closer and touched her arm. "Are you okay?"

Blair lifted her chin defiantly and pulled her arm away. "Yes, I'm fine. Stop deflecting and tell me why you're here," Blair demanded.

Dan shrugged his shoulders. "I just wanted to see if you were free to watch a movie or something."

"Well, I can't. I have a date and he should be arriving any minute. Now if you'll please excuse me, I need to go to my room to freshen up," Blair told him

He felt his chest tighten and a pang of jealously hit him. Why did he even care? She was Blair Waldorf, Queen B of Constance. They were barely even friends.

"With who," Dan asked

He was so distracted with his thoughts that he didn't even hear the elevator ring.

"Hey beautiful."

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**I'm sorry, I know you guys hate me right now. R&R and tell me how much :)**


	4. Chapter 4

**A/N: I wanted to thank everyone for the reviews and apologize for the confusion. Unfortunately, the reviews were deleted, but I got to read the reviews through my email so thank you. Also, since this story was deleted, the people who decided to follow this story will have to follow it again to be alerted. I still have a good amount of chapters left to post.**

**Lastly, I wanted to point out that this story doesn't follow the season 1 timeline.**

* * *

_Hey beautiful_

Dan spun his heels and found the suave Carter Baizen holding peonies in a white dress shirt tucked into his ash grey slim fit pants.

"Dan Humphrey," Carter said with a smirk

"You two know each other," Blair asked furrowing her brows in confusion

He recalled meeting Carter while playing basketball with Chuck and Nate. He later discovered Nate had spent the night playing high stakes poker with Carter only to learn that he had been set up.

"Nate's going to be upset your here," Dan told Carter

"I'm sure he will be, he got played," Carter said. "But that doesn't mean you should be. Me and you have a lot more in common than you think."

He's heard stories of how Carter Baizen didn't accept his parent's trust fund and went hunting for treasure. Some said he left the UES to backpack in Europe to discover himself. All of those rumors were fictitious and gave him too much credit. In reality, Carter was in a shit load of trouble and had a large gambling debt.

"Because we're both outsiders," Dan concluded leading Carter to smile. Dan turned his head to Blair. "I'd make sure to keep your jewelry in a safe, other than that, have fun."

Dan then headed out of Blair's penthouse wondering what the hell Blair was thinking.

**XOXOXOXO**

Dan spent the next few weeks surprisingly gloomy. He told Nate about Carter which made Nate furious. Chuck sent a P.I. to investigate Carter's past while Serena was telling him about how Carter was just using Blair and she was setting herself up to get hurt. It seemed Blair didn't care, as long as she expected to get hurt, she was fine with it.

He tried to ignore the drama and spent most of his time in the loft writing. His schedule consisted of school, working at the coffee shop, soccer, classwork, and writing. All of his feelings were written onto his notebook. His father began to worry while Nate and Serena kept calling, but he continually ignored them. He didn't want to go out and get wasted so he could escape his emotions. He needed to figure out what these feelings meant, and in the end, it only led him to one conclusion.

He had feelings for Blair.

As he sat in his room writing on his study desk, his phone vibrated. For the first time in weeks, he received a text message from Blair.

_Blair: Having people over at my place ;)_

He groaned in annoyance and rolled his head back as he ran his hands through his hair. Partying was the last thing he wanted to do. He had just came back from a soccer game and his whole body was sore. He could just ignore her like he had been doing with everyone else, but for some reason he had trouble saying no to Blair.

**XOXOXOXO**

Entering the Blair's foyer, the guys were wearing loafers with button downs or sweaters that cost more than his bed. He himself went with a simple grey long sleeve Henley and black pants. As he entered the living room, he found Blair chatting with Carter leading him to feel a sting course through his heart. His solution for being able to get through the night was alcohol and finding someone to take his mind off Blair.

Stepping into the dining room, he found Nate mixing hard liquor with some fruity drink into a large red plastic cup. Nate was wearing a blue blazer with a yellow button down underneath. It was still amazing to see how overdressed these people were. Sometimes he just wished he went to a regular school with normal people so he wouldn't feel so out of place.

"Dan, you're actually here," Nate said looking surprised. He then handed Dan the liquor bottle leading Dan to take a swig from it. "Whoa!" Nate's eye's widened in amusement. "You alright there buddy."

"I'm fine," Dan replied pouring himself a drink in a red plastic cup on the side. "Where's Serena?"

Nate frowned. "She's out with a friend."

Dan glanced over to Nate who seemed a bit distressed. "Is everything alright?"

"Serena's becoming distant and my parent's marriage is waning, not much is looking up for me," Nate said looking more brooding then Dan had ever seen him.

"I'm sorry man."

Nate looked up and shrugged his shoulders. "My dad's been pressuring me to get back together with Blair. He desperately needs the business deal with the Waldorf's to work out."

Dan leaned his back against the dining room table while taking a sip from his cup. "Wow," Dan stated in disbelief. "Have you told Serena?"

Nate shook his head. "What's the point when I can feel her drifting away?"

He had no idea Nate's relationship with Serena was in trouble. He was so consumed with himself that he wasn't paying attention to the people around him.

"I miss Blair," Nate admitted quietly

_Fuck my life_

"I made a mistake," Nate added

"That's completely understandable, you guys had been together forever. I'm sure she misses you to. She has to be," Dan reassured Nate after clearing his throat.

"You can't tell anyone, you know a nuclear war would occur if Serena found out," Nate said

"Of course, this stays between us."

Nate leaned his back against the table as well and took a sip from his red plastic cup. "I think Chuck has feelings for her as well," Nate confided in him leading him to perk up and raise his brows. "He's been in my ear about loving Serena for the past 2 years."

"Maybe Chuck's just trying to be a good friend."

"He was the one who ratted me out to Blair about sleeping with Serena," Nate said with his jaw beginning to clench. "He was apparently watching us having sex at the Shepherd's party." Nate shook his head. "Blair finally told me how she found out last night."

"I don't know what's worse, Blair dating Carter, or dating Chuck," Dan replied. "Have you talked to Blair about Carter?"

"I've been trying to, but she says I have no right to speak to her about who she dates," Nate explained.

Carter was clearly up to something because he was running low on cash and he had already stolen Chuck's watch and autographed baseball.

"I'll talk to her man."

Nate nodded before Dan headed out of the dining room.

After talking to Nate, he walked away thinking he needed to move on with someone else so he could get over Blair and not become involved in this strange love pentagon.

Chatting with Emma in the kitchen was helping him keep his mind off Blair. Her black hair shined and her amazing long tan legs stood out. She was of course as well put together as the rest of the girls in Constance were. They had nothing in common other than the fact they both played soccer and it was how they met, they would talk at times in between soccer practice.

"So I heard you scored today," Emma said

"Yup, first and probably last time," Dan replied before licking his lips and smiling.

Emma giggled. "You're not that bad."

"Humphrey! What a surprise," Blair said leading Dan to turn around and find her standing by the doorway of the kitchen. "What are you wearing?" Blair scrunched her nose and then looked at Emma. "By the way, Leslie was looking for you, she said something about meeting her in the guest bedroom."

Dan's tilted his head and knitted his brows together. "Really, so this girl conveniently told you that we were planning to meet in your guest bedroom."

Blair just shrugged her shoulders batted her eyelashes looking as innocent as possible. "I suppose she's very drunk."

"I don't even know a Leslie," Dan exclaimed getting annoyed

Blair was glaring at Emma leading her to become fearful. "I should go, it was nice talking to you Dan," Emma said and scurried out of the kitchen like a deer hearing footsteps, leaving Dan with Blair.

He watched her step closer while pursing her lips and smiling like she was victorious. "What the hell was that," Dan asked

"I was just saving you from making a mistake. I heard she's pretty hairy down there," Blair said pointing to down with her finger.

Everything came back to sex to these people. They don't understand that he was just trying to get to know her, and if they kissed, it would only be considered a plus for him.

"Why do you care," Dan inquired

"And I heard it smelled like tuna," Blair added ignoring his question while wrinkling her nose in distaste.

Dan shook his head. "Now you're just being mean," Dan said leading Blair to giggle. "Are you drunk?"

"Just a little," Blair replied demonstrating how small with her fingers. She then slowly pressed her back against the counter and he could notice her trying to lift herself up onto the counter but was having difficulty with it. He gently grabbed her waist and hoisted her up to place her onto the countertop. "Thank you."

"Shouldn't you be with Carter instead of trying to ruin my life," Dan asked

"But I like torturing you more," Blair teased and began playing with the buttons on his Henley. "You've been distant," Blair said quietly

"I've been busy," Dan told her as he noticed her yellow headband matching her yellow half sleeved blouse and contrasting perfectly with her white skirt.

"You don't seem happy with me dating Carter."

"That's because I don't think he deserves you," Dan explained meeting her eyes

"No," Blair asked softly

"No," Dan confirmed softly

As he met her eyes, all could think about was leaning in to meet her glistening pink lips, wanting to memorize the flavor of her lip gloss. But instead, he chose to touch her cheek with his hand and stroke it with his thumb.

"Do you know how special you are," Dan asked leading Blair to intake a sharp breath and look down as she melted into to his touch. "If you could only see what I see."

Blair's head tilted up to meet his eyes. Her eyes were softening and her full lips were beginning to quiver. He slowly slid his hand away and sluggishly stepped back towards the foyer while taking in the image of Blair with her guard down.

Walking into the foyer, he was planning on leaving. He decided it was a waste of his time to come to the party. It only made him fall harder for Blair and the only solution he could think of was distance. If Nate was being honest about his feelings for Blair, then Dan knew he didn't stand a chance with her. Nate was her prince, her fairytale. They were supposed to get married, it was set in stone.

The elevator door opened to find Serena walking in with her arm draped around the neck of a blue-eyed, pale skinned, dark haired brunette. They were laughing hard and both girls seemed to be tipsy.

Serena beamed once she saw him standing in the foyer. "Dan! You're here!"

"Well it's not everyday you get invited to a party thrown by Blair," Dan said with a smirk as he shoved his hands in the pockets of his pants.

The brunette was wearing heavy duty jewelry and the ring on her finger was unnecessary large. Her eyes were big and she could pull off the innocent act, but after watching her walk into the foyer in Serena's arms, innocent was the last thing he would call her.

"Who's this lug of meat," the brunette asked leading Dan to raise his brows

Serena giggled. "My future stepbrother."

"Well this night just got interesting," the brunette said. He watched her scan over his body and he started to become slightly uncomfortable. "Where's the alcohol," the brunette asked

"In the dining room," Dan replied

As he watched her head out of the foyer and into the dining room, he realized there was one thing for sure, this night just got interesting. He wasn't planning on leaving after witnessing that.

"What's her name," Dan asked

"Georgina."

Leaning his shoulder against the doorway of the living room with Nate by his side, he watched Georgina dance with Serena. The girl was insane, she already pulled Nelly Yuki in for a kiss while her eyes were on him. She then chugged a half a bottle of Blair's ancient wine, which led Blair to be furious since the wine was over 60 years old. The best part of the night was Georgina and Blair bickering at each other. It's always amusing to watch two bitches verbally sparring.

"What is that," Dan questioned as he was watching Georgina's legs wrapped around Serena's waist while her both her hands were on the carpeted floor and her back was arched with Serena dancing against her.

Nate laughed. "She's crazy man. You know she took Chuck's virginity in the sixth grade." Dan looked over at Nate with a look of incredulity. "Explains a lot, doesn't it."

Dan glanced over and found Blair glaring at Georgina. She then noticed him staring at her and met his eyes leading her features to soften. He was pleased and surprised to have that effect on her. After taking a sip from her wine, she stared at him intently as though she was absorbing every ounce of him. His chest began to tighten and he felt his cock twitch when she licked around her lips while staying on his eyes.

Dan turned to Nate. "I think I'm going to head out."

"What? Dan, it's only 11:30."

"Humphrey. Surprised to see you come out of your shell," Chuck said as he walked up to Nate and Dan from the foyer. "You've probably heard Nathaniel is quite upset with me."

"Yes, he told me about your obsession with Blair," Dan replied wryly

Chuck stared at Blair. "She's a rare breed Humphrey, I imagine her tasting like honey." Chuck turned to Nate. "It's sad Nathaniel wouldn't be able to confirm that for us."

Nate's jaw clenched as his eyes began to resonate with rage. "I'd shut up if I were you."

"You had her and you lost her, she's fair game. Besides, you could never satisfy her in the way I can." Chuck then leaned in towards Nate. "I would have her screaming all night."

Nate then shoved Chuck to the ground of the marble floored foyer. "What's your problem man," Nate yelled leading everyone's attention to fall on him.

Nate's a fool. This was exactly what Chuck wanted. From spending time with Chuck, he's learned everything was a mind game. Being physical wouldn't do anything.

"Nate!" Blair scolded as she walked across the living room into the foyer. "Are you out of your mind?"

"I'm outta here," Nate murmured to himself bitterly once he stepped over Chuck to head towards the elevator with Dan following his every step.

After they left the Waldorf penthouse, Nate took him back to his townhouse where they tried to play _Call of Duty _but the yelling and screaming of the Captain and Anne Archibald was heard through the walls. Nate looked ashamed while he felt uncomfortable. It was then where Dan realized there was so much more to Nate then people realized. He was a natural leader and felt a burden of responsibility to keep this family together. Eventually, the clock struck past one and they both decided to get some sleep. Nate slept on his bed while Dan slept on the couch in his room dreaming of a chestnut haired brunette.

**XOXOXOXO**

A week had passed since Blair's party. He was sitting on the bed with his back pressed against the brick wall, staring at the invitation to the Masquerade Ball. His plan of avoiding Blair was an epic failure so far. Much to the class's protest, he was paired off with Blair for their English project. Everyone was upset they would ruin the grading curve while he was feeling woozy just thinking about spending time alone with Blair.

"Dan?"

Dan looked up to his fire escape and found Vanessa stepping into his room through the window. She was even more gorgeous then he remembered. He slid off his bed and stood in front of the dark haired brunette.

"Wow, you've grown," Vanessa said with shock resonating in her voice

"Me? Look at you, you look great," Dan replied gesturing with both his hands. "What are you doing here anyway?" Dan smiled

"I'm moving in with my sister," Vanessa explained tilting her head. "This isn't awkward right? Me springing up on you?"

"Of course not," Dan said smiling and shaking his head. "You have no idea how much I missed you."

"Really," Vanessa asked sounding hopeful

"Vanessa," Jenny shouted ecstatically

He watched his sister run into his room leading them both to hug and squeal. His father on the other hand remained calm and gave her a warm greeting.

Sitting on the stools by the kitchen counter, they sat on a Saturday morning enjoying his father's waffles. The Masquerade Ball was still on the back of his mind. Since Vanessa was here, he was leaning towards not attending. It would be a good way of avoiding drama for the night. Nate had broken up with Serena and he didn't want to have to witness Nate making a move on Blair with Serena watching. It was one of the things he missed most about Vanessa, there wasn't any drama.

His phone vibrated and a text message appeared from Nate.

_Nate: Can I come over? My father's in trouble_

_Dan: Yeah, the loft door is unlocked, come straight to my room_

"Nate's coming over," Dan stated as everyone was enjoying their waffles.

"Who's Nate," Vanessa asked

"Only the best looking guy attending St. Judes," Jenny explained. "He has these dreamy blue eyes and perfect blonde hair."

"Which takes him hours to maintain," Dan added

"Nate? That's Serena's boyfriend right," Rufus inquired

"Ex actually. They broke up a couple of days ago. There are rumors flying around about Serena being a lesbian with Georgina," Jenny told them leading Rufus's eyes to widen

Dan stuck his hand out to stop the madness from continuing. "Okay, stop freaking Dad out with these senseless rumors. The truth is that their relationship was based more on physical attraction than anything else, and it just fizzled out."

They heard a soft knock on the loft door and Dan went to see who it was. He opened the door to find Blair on the other side standing in her Burberry London Wool Kimono-Sleeve Cape jacket.

"Humphrey," Blair stated simply while stepping in without an invitation. Her eyes glossed over to the counter where everyone was eating. "Hi."

Dan followed her eyes to Vanessa and a fake smile began to creep up on her lips. "That's Vanessa," Dan pointed out.

"Nice to finally meet you, although Humphrey has never spoken a word of you," Blair said scanning over Vanessa. "You must not be that important," Blair said indifferently and Vanessa's jaw dropped as Blair went into Dan's room with her chin high.

Dan smiled uncomfortably. "That was Blair."

Following Blair into his room, he made sure to close the door to his room since he knew how nosy Jenny could be.

"You didn't have to go all Blair on Vanessa," Dan said trying to sound mad, but he just sounded weak. He couldn't be mad at her, especially since it gave him hope that she was being territorial.

Blair rolled her eyes. "What are you wearing tonight," Blair asked ignoring his comment. She looked around and began studying his room.

"You came here to ask me what I was wearing for the Masquerade Ball," Dan inquired with a smirk. "There is a thing called cellphones Waldorf." Dan stepped closer, invading her space and noticing her recoil slightly. He hated how her heels would keep them on the same height level. "To answer your lame question, I'm leaning towards not attending."

"But you have to attend."

"I don't have to do anything. Besides, I recall you saying I wasn't worth wasting posh paper on. So why does it matter," Dan said.

"I was wrong for saying that."

Dan tilted his head playfully and gave her a smug grin. "You were wrong because….."

It was amusing to watch her struggle. It was as though her admitting they were friends was like him having to tell someone they had cancer.

"Because….Because." Blair drew a deep breath. "Because we are…Friends," Blair murmured quietly

"Geez, try not to have a stroke Waldorf," Dan said with a smile. "Now that you're being honest, tell me why you're really here." He could see her still having trouble with her attempt to avoid his eyes. Dan lifted her chin with his fingertips and met her eyes. "You can tell me anything. I'm not like the others. There's no motive with me."

Blair slipped away from his fingertips and stepped back. She looked frightened and timid. "I have to go. Come to the masked ball or I'll have your head," Blair said tersely as she scurried out of his room and the loft while he was left scratching his head.

After they finished eating, Vanessa sat on his bed crossing her ankles while Dan was sitting on his desk chair facing her.

"So have you dated anyone since…"

"Since I told you I loved you," Dan interrupted Vanessa leading her to nod shyly. "No. You?"

"Yes, but nothing serious," Vanessa said looking down and playing with the hole on his blanket. "Couldn't get over me," Vanessa teased leading Dan to raise his brows. "Too soon?"

"There is someone that's been on my mind."

"Oh," Vanessa replied looking disappointed

Dan knitted his brows together. "What's wrong?"

"Nothing, tell me about her." Vanessa looked up to meet his eyes, attempting to mask her disappointment.

Dan bit his lower lip thinking before speaking. "I have feelings for Blair, the girl who was just here."

"The elitist who said I was insignificant and then ran off acting as though she had just been infected with some disease," Vanessa said looking at Dan incredulously. "You sure know how to choose them Dan."

"Vanessa," Dan groaned rolling his head back

He felt a bit worried sharing his feelings for Blair to Vanessa. Vanessa was judgmental and hated everything about the Upper East Side, but there wasn't anyone else he could to speak to about it. With Vanessa, there was no way their conversation would get out in school or in his social circle.

"I just think you're setting yourself to get hurt, you don't belong in their world," Vanessa reasoned softly.

"You think I want to feel this way? You don't think I understand that we're from different worlds," Dan asked looking at Vanessa in disbelief. "These feelings are killing me. I'm in agony here. My best friend is in love with her and I'm going to have to watch him sweep her off her feet."

"Wow, I'm sorry Dan, I didn't know how much you liked her."

Dan slide off his chair and stood up. He reached out for a box in his dresser and tossed it on the bed. Vanessa arched a brow and opened the tiffany's box to find a sterling silver oval lock pendant. Vanessa looked pulled out the eighteen inch chain necklace and found the words _Always in my heart, together or apart _inscribed on the back of the locket.

Vanessa glanced over to Dan. "How much was this?"

"550 dollars," Dan said running his hand through his hair nervously.

"Dan!" Vanessa scolded Dan. "How could you even afford this?

"I've been working at the coffee shop down the street and had been trying saving money for a laptop," Dan explained standing at the edge of his bed. "Blair's birthday's next week so I spent it on the necklace instead."

"Are you insane," Vanessa yelled. "This isn't even something you would do. The Dan Humphrey I know doesn't give jewelry as a gift. He's more sentimental."

Dan sighed in defeat. "I know, I'm pathetic." Dan plopped back down of his chair.

**XOXOXOXO**

It was everywhere he looked. The Captain was being charged with embezzlement and fraud. The previous night, Nate had came over to the loft and began telling him of his father's troubles. It felt like he was listening to Nate drop everything off his chest. He was shocked listening to Nate's revelations. The Archibald's, considered royalty to some, were having money problems. It was even more surprising to learn of his father's drug issues. Nate had just recently found a plastic druggie bag of cocaine in his father's cabinet.

Nate pleaded with him to attend the Masquerade Ball, stating that he didn't want to be alone. Dan decided against it, explaining that he was planning on attending a concert with Vanessa. Once he woke up the next day, he discovered Nate's father had been arrested.

For the rest of the week, Nate began sleeping over at his place. Nate couldn't stand to watch the bank and the feds take his family's possessions. It led his mother to be in tears and his father to become overwhelmed with guilt.

As the days passed and they inched closer to Blair's birthday, Nate started becoming more and more anxious. The Archibald's didn't have any money to spend and Nate couldn't give Blair his family ring. It was a symbol of the business deal. Dan thought Blair would understand and he could've given her something more sentimental, but Nate wanted to give her something that would help him win her back. Nate told him Blair valued jewelry more than anything. He disagreed, he always found Blair to be more of a romantic, but how could he argue with someone who dated her for his entire life.

The night before Blair's birthday, Dan made a decision to help his friend.

"You should give this to Blair," Dan said standing in his room while handing Nate a Tiffany's box.

Nate opened the box and reached for the necklace. "Always in my heart, together or apart." Nate read the inscription.

"I knew you wanted to give something special to Blair, so I bought this necklace for you to give her," Dan explained

Nate tilted his head up. "I can't accept this."

"You can. I know you're good for the money," Dan told Nate. "Besides, you would do the same for me."

Nate smiled in disbelief. "I don't know what to say."

Dan reached out to touch Nate's shoulder with his hand. "Tell her you love her and that Serena was a mistake."

Nate was a good guy who would treat Blair right if he had been given another chance. They seemed to be in love before Nate's mistakes and he could see how much Nate regretted his decisions. Unlike him, Nate could fulfill all of her dreams. Nate was everything she wanted.

* * *

**I know it might be surprising that N/S didn't last but they didn't last on the show either. They seemed to have fizzled out so I was staying true to that. I do think it's plausible for them to be endgame, but I didn't think it would make sense in this story because they're so young right now and Serena likes to date around, her character doesn't seem like the settling down type. Besides, I always felt Nate loved Blair more.**

**R&R are always welcomed**


	5. Chapter 5

**A/N: Thank you for the reviews and follows. All I will say is that this chapter goes with the M rating. Don't want to spoil anything, but I just wanted to warn the readers.**

* * *

Dan decided against attending Blair's birthday party. He knew she'd be upset with him for not attending, but watching her fawn over Nate was something he could do without. Before Jenny left for Blair's, Dan handed her a short story he'd written with a note attached to it stating, "_This is what I see."_

Tossing and turning on his bed, trying to get some sleep in the middle of the night, his phone buzzed. He glossed over to discover a text message from Blair.

_**Blair 1:49 A.M:**__ You're an asshole and I hate you. Don't ever speak to me again_

At least it was going to be easier to get over her now

**XOXOXOXO**

Staring at the wall and listening to the Rolling Stones while lying on his bed, he continued to ignore the knocking. He couldn't write anymore and it felt as though there was nothing that could lift his mood. His heart felt heavier than it had ever before and he didn't have much of an attention span because it would go back to her.

_How do you kill a feeling?_

Time and seclusion was his solution.

"Dan! Please, open the door," Jenny pleaded with desperation resonating from her voice.

He started to worry and rushed to his door to unlock it. Opening the door, he found Jenny in tears, mascara running down her cheeks. She instantly wrapped him into a hug and cried on his shoulder. He carefully led her to his bed where she continued to cry into his chest.

"Jenny, what happened," Dan asked softly caressing her back with his hands and kissing the top of her head.

"I..I slept…with Chuck," Jenny sobbed. "After Blair's birthday party, he took me to his suite."

"and," Dan probed softly

"I woke up in the suite and he just treated me like one of his whores," Jenny said against his chest. "When we reached his suite, I wasn't even planning to sleep with him, but then everything became hazy and one thing led to another. I was more drunk then I had initially realized."

It was clear Jenny didn't have a clue as to what really happened to her and he wasn't going to tell her. He didn't want his sister to be scarred. Chuck had his victims, he would slip a pill into their drink, it was one of the things everyone overlooked. To his peers, Chuck could do no wrong. It disgusted him while everyone just accepted it.

"I really liked him. I didn't think he would do that to me," Jenny admitted softly. "You're all I have Dan, the only person I can trust. These people are toxic."

"Shhhh…I know." Dan held on to her tightly rocking her back and forth.

**XOXOXOXO**

Sitting on the Met Steps with Serena, he glanced over to find Jenny not sitting with Blair, but instead with a different group of girls. Jenny had changed since the incident with Chuck. It seemed to have only made her stronger. He could see it in her eyes that she was out for revenge.

"Did something happen between Blair and my sister," Dan asked looking over to Serena on the steps.

"Not that I know of," Serena said shrugging her shoulders while holding a yogurt. "Are you coming to dinner on Sunday?"

"I don't know. Is Georgina going to be there?"

Serena laughed. "So what if she is?"

"Why do you invite her," Dan groaned rolling his head back in annoyance. "She's insane. I spent the whole time pushing her foot off my crotch during our last family dinner."

Serena nudged her shoulder against Dan. "Come on Dan, maybe Georgina is exactly what you need," Serena teased.

Dan shook his head and then realized Blair was walking down the steps towards them. She hadn't spoken a word to him since the angry text message and he was feeling a bit anxious as she drew closer. She was holding a smile which was difficult to decipher between evil and arrogant.

"Humphrey, we need to work on our project," Blair told him while she towered over him. "I want to finish it before Thanksgiving."

Dan pulled his messenger bag over his shoulder and stood up. "Okay, why don't we split up the work, and then we can meet sometime before Thanksgiving to make the PowerPoint."

He noticed she wasn't wearing a necklace he bought which was puzzling. Maybe she didn't like it because she's accustomed to more extravagant necklaces. He wondered how Nate felt about that.

"Don't be silly, come over to the penthouse after soccer practice and we can share our notes on _The Age of Innocence_," Blair said tersely with her hand on her hip.

Dan raised his brows. "I thought you hated me."

"I do. So very much," Blair replied with a fake sweet smile. "But that doesn't mean I'm going to let you ruin my GPA."

Once soccer practice was over, he took a shower in the locker room and changed back to his St. Jude's attire to leave for Blair's. Going to Blair's was the last thing he wanted to do. It was clear she was still upset with him for being a no show to her birthday party, but he thought his story would have at least softened her stance. It probably meant she didn't even read it.

Dorota led him into the living room where he found two yoga mat's set up. As he sat on the couch, an older man walked in with a tank top and shorts, holding a water bottle. Once the soothing yoga music began playing, he realized the man was a yoga instructor.

"Humphrey," Blair stated simply walking into the living room while holding a notebook. She was wearing a white tight tank top and skintight black tights.

Dan swallowed nervously feeling the beads of sweat forming. "What's the deal? Should I come back later?"

Blair handed him her notebook. "No, you came here at the perfect time," Blair said leading Dan to arch a brow. "Read over my notes and we can discuss them once my yoga session is over."

"You couldn't have chosen another time to do this," Dan inquired as he watched Blair sit down and stretch on the mat.

"Nope," Blair replied accentuating the "p".

It wasn't difficult to keep his attention on her notes in the beginning since Blair was only doing basic seated and twist poses. Unfortunately, his attention steered towards Blair once they started going into more advanced techniques. She was doing backbend poses he didn't think were humanly possible. It felt like she was punishing him. He didn't understand why she couldn't have worn regular sweatpants as he saw her hips stick out while she was in the _Dolphin Pose_. Instead of watching her in sweatpants, he was stuck staring at her butt cheeks screaming to be released from her tights which was leading him to fight against his urges.

After a painstakingly long and agonizing workout, they finally went up to Blair's room. Once she had finished reviewing his notes, he started writing their paper on her laptop. They would bounce ideas off each other and he was reminded of how intellectual she truly was. She was the only person he knew who could match his wit.

Dan sighed as he sat against her headboard with her laptop on his thighs. "So all we have left to do is the introduction and conclusion," Dan said turning his head to meet her eyes.

Blair beamed. "Not bad Humphrey, we're ahead of schedule."

"And we could probably start filling in the PowerPoint right after we finish the intro and conclusion."

"Leaving us only having to practice our presentation," Blair added.

Dan slid off Blair's bed and picked up his messenger bag. "So I'll edit what we have written later tonight, and then email it to you so you can edit it as well."

"Sounds like a plan."

"Okay, see ya."

"Wait," Blair said leading Dan to stop and face her. Blair began playing with the edge of notebook avoiding his eyes. "Are you going to the Crowne's fundraiser this weekend?"

"No, but I'm sure Nate will be there," Dan replied giving her a light smile.

"And Lily won't be upset for your lack of attendance?"

Dan knitted his brows together. "Aren't you supposed to be mad at me?" Blair pursed her lips and folded her arms across her chest. "Is everything okay?"

"Perfectly pleasant."

"Well, then I should get going."

_She's acting strange_

**XOXOXOXO**

It was Sunday night, meaning dinner at the Van Der Woodsen's. Lily hated it because she would have to help his father cook, but he could tell that was an act. On the inside, Lily enjoyed it, he couldn't count the amount of times he would hear a laughter ringing from the kitchen.

"God! I'm bored," Georgina groaned impatiently and then a devilish smile appeared on her lips. "I know, let's play spin the bottle."

"You do realize Eric and Serena are related," Dan said

Georgina arched a brow. "So?"

Dan grimaced while Georgina laughed like a villain would.

"Oh come on Dan, she's just teasing you," Serena said sitting next to Georgina on the couch.

Dan was left scratching the back of his head thinking this was going to be a long night.

The rest of the night at the Van Der Woodsen's consisted of listening to his father's romantic tales with Lily while he was pushing Georgina's hand off his thigh. He had to admit, he was actually happy to have Georgina there because the night would have been pretty dull otherwise.

"I heard what Chuck did to Jenny," Georgina said by his ear while the rest of his family were discussing about the Obama and McCain election.

Dan turned his hips to face her. "So?

"Let me help you get Chuck back."

"What do you want in return," Dan asked quietly. "And no, I'm not having sex with you in the bathroom."

"Listen, I don't want anything, I actually feel sympathy for your sister."

Dan smirked. "Sympathy and you don't mix."

"Do you want my help or not?"

Dan sighed in defeat. "Okay, I would do anything to get back at Bass."

Georgina's eyes lit up. "Perfect, I've been planning this for a couple of days now. I'll pick you up outside your loft at 1."

"Don't come to the loft. I'll be at Blair's finishing up our project and since my Dad is staying here for the night, I won't have to go back to the loft."

A wicked grin appeared on Georgina's face and he knew he was in a load of trouble.

**XOXOXOXO**

After dinner, he caught a cab straight to the Waldorf Penthouse. Once he reached the foyer, the first thing he noticed was how unusually warm it was. It led him to take his jacket as well as button down off to be only left with a white t-shirt. There was light shining through the dining room and it was there he found Blair writing on her laptop wearing an half sleeved button down black blouse.

"Have you started on the introduction," Dan asked leading Blair to raise her head and meet his eyes. She nodded in response to his question and he pulled up a chair to sit next to her while taking in her scent. Before he met Blair, he always felt Chanel No. 5 was overrated, but now, he doesn't think he could go a day without catching a whiff of it.

After they finished writing the introduction and conclusion, they were left with working on the PowerPoint. It took them a couple of hours but they were able to finish once the clock struck half past midnight. The whole time they worked, it was unbearably hot. His hair was damp and sweat was trickling down his forehead. Blair's reasoning was that the central heating system was broken.

Blair began fanning herself with her hand and there was a bucket of ice by her side on the table. "God it's hot," Blair said unbuttoning her blouse leading Dan's eyes to widen at the sight of bare skin. He tried to keep his eyes on the screen of laptop as he edited their paper. "Dan?" Dan looked over to find Blair only inches away with her chest touching his arm and her lips sucking on a cube of ice. "It should be there, not their."

"What," Dan asked with his voice cracking as his eyes fell to her cleavage where a visible purple bra appeared. His eyes then fell back up to Blair's mouth and found her lips curved into seductive smile.

"T-h-e-r-e." Blair spelled out as he could feel her breath on his lips.

"Oh," was all Dan could muster out as his eyes went back to the laptop.

"Dan?"

"Hmm."

"Are you okay," Blair asked breathing on his neck with her hand pressed against his chest. "It feels like your burning up." His eyes left the laptop to find her continuing to suck on a cube of ice. He watched her take the cube of ice from her mouth and put it into his. "Better?" Blair breathed

He couldn't fight against his hormones any longer. While having the ice still in his mouth, he stood up and hoisted Blair onto the dining table earning an excited squeal. Finding half of her top unbuttoned, he leaned in and slid the ice across her chest with his mouth leading Blair to gasp. While sliding the ice over her bare skin, he felt her unbutton her shirt under his stomach.

Pulling away from her chest and spitting the ice back onto the dining room floor. He saw her eyes filled with lust and need as she splayed across the wooden dining table with her heels tugging his hips closer. He grabbed her hips and pulled her to the edge of the table for their pelvis's to be pressed against each other causing a whimper to escape her lips. As she tossed her shirt aside to be only left with a bra, Dan lunged towards her and began kissing her feverishly with his hands running through her chestnut hair. He then moved his lips to her neck leading her to moan and slide her hands under his shirt.

"I wanted you for so long," Dan murmured against her neck making her moan louder with her nails raking against his chest.

"I want more," Blair said softly as she wrapped her arms around his neck and pulled him closer.

He began to slide his hand down her thighs and felt her breathing becoming heavier.

"Are you a virgin," Dan asked softly teasing the small ribbon of her lace panties with his fingers.

"Yes," Blair replied with an impatient tone of voice and her lips on his jaw.

"What about your hymen?"

"It's been broken." Blair pulled away and met his eyes

"Tish tish, you're naughty Blair Waldorf," Dan teased with a smirk leading Blair's eyes to flare.

"Dan," Blair groaned in annoyance

Dan cupped her cheek with his free hand and met her eyes. "I'm sorry, I didn't mean to embarrass you, I just want to make sure I won't hurt you," Dan explained softly.

Her features softened and she reached for his cheek. "Thank you," Blair said softly and then pressed a soft kiss on his lips.

Sliding his hands under her lace panties, he began to rub the outside of her entrance leading Blair to bite her lip. Once his fingers inserted through Blair's entrance, she leaned in and moaned against his mouth. He couldn't believe how wet she was. Just as he began stroking in and out gently, the elevator dinged.

_Georgina's early_

Everything was a blur after. He stepped aside rapidly, leading Blair to slide off the table to find her shirt. They were collecting themselves in a hurry, but surprisingly, the visitor took some time to reach them.

Thankfully, Blair was able to button up her blouse and straighten out her headband before Georgina reached the dining room.

"It's boiling in here," Georgina said as she reached the dining room.

"Yeah, Blair's central heating system is broken," Dan told Georgina

"No, it's not, I just lowered the temperature on the thermostat," Georgina replied. Dan narrowed his eyes over to a smirking Blair. "Come on Dan, we're going to be late." Georgina then headed towards the elevator leaving Dan alone with Blair.

"How high did you have the temperature," Dan asked furrowing his brows in confusion.

Blair ignored his question and reached for his hand as she stepped closer. She then took the two fingers that were filled inside her and slowly placed them inside her mouth to suck on them, staring into his eyes intently. His jaw dropped and all he could think about was placing her on the table again.

Pulling her fingers away from her mouth, Blair said, "Come over tomorrow after soccer to practice our presentation?"

"Yeah," Dan replied hoarsely

**XOXOXOXO**

Sitting in the passenger's seat of Georgina's silver Chevy Cobalt, he looked around and realized how disgusting it was. There were cigarette cartons and empty bags of chips on the floor. It was like she had a party in here.

"I never imagined someone from the UES owning a Chevy," Dan said glancing over at Georgina eating out of a bag of Cheetos's.

"Staking out with my beamer would be foolish, we need to be hidden, there is no need to attract attention," Georgina explained

"I'm going to take a wild guess and say this isn't your first stakeout," Dan replied wryly. "I don't think I'll ever be comfortable at the sight of a silver Chevy Cobalt again."

"Welcome to the Upper East Side, where people betray, stalk, fuck, and lie," Georgina said smirking leading Dan to grimace. "I try to find out as much as possible about these people."

"Why?"

"There's nothing more powerful than information," Georgina told him and leaned in. "I know everything Daniel," Georgina whispered.

Dan's lip curved slightly. "Do tell."

"Well I can see how hard our own Queen B has fallen for the penniless writer from Brooklyn."

"I think she likes me, but falling hard is a bit of a reach," Dan disputed shaking his head

"How can you not see it? She wants a taste of Brooklyn." Georgina smirked. "And I don't blame her."

Dan chuckled and looked out the window. "I hope so."

"Anyone with eyes can see that you're madly in love with her," Georgina said leading Dan to turn his head back to her. "And she isn't far off from feeling the same way. I could argue it's more even."

"I don't believe you."

"That's because you haven't been paying attention. But if you're having trouble believing me, look around your room, there might be a clue."

Dan ran his hands through his hair and took a deep breath taking in everything Georgina had told him. He had trouble believing the malevolent dark haired brunette. She was insane and was probably fucking with him.

"Vicodine," Georgina offered Dan as she held out a plastic orange prescription bottle

Dan knitted his brows together. "You carry a bottle of Vicodine with you?"

Georgina shrugged her shoulders and popped a pill into her mouth. Her eyes then widened as she spotted Chuck walking in the arms of a blonde across the street. "There he is, it's working."

"This is your plan, to get Chuck laid," Dan said dryly

"That girl isn't just any random bimbo. This specific girl has gonorrhea."

"You're plan is to get Chuck an STD?" Dan shook his head at the ridiculousness of the situation. "How did you even get the girl to say yes to this," Dan said and then put his palm out. "You know what, I'm don't want to know."

Georgina pointed to Chuck pressing the blonde against the wall. "Look!"

"I have a feeling we're going to get arrested."

"Relax, he'll have no idea this had something to do with us. He's clearly wasted and won't even remember the girl's face," Georgina told him. "So there is nothing to worry about."

"Except I'm going to be having to live with the guilt of Chuck not being able to piss for months," Dan replied

"He took your sister's virginity without consent."

Dan's jaw clenched and he looked to be in deep thought.

_Fuck it_

**XOXOXOXO**

Georgina's plan had worked. It was cruel, but what Chuck did to his sister was cruel as well. This was what the Upper East Side does, it's toxic and it brings out the worst in people. His sister was exhibit A, she went from a soft caring, fun-loving girl, to a cold hearted person trying to bring down anyone who stood in her way.

Sitting on the wooden bench of his locker, he waited for Nate to change into his practice gear. He was supposed to go to Blair's after practice and being around Nate made him feel guilty. Nate was in love with her, he dated her first and would be furious if he found out about last night.

"So how's it going with Blair," Dan inquired tightening his shin guard.

After Nate gave Blair the necklace, he spent the past week trying to spend as much time with her as possible trying to get on her good side again.

"It's hard to get a read on her, she's Blair you know, keeps everything close to her chest," Nate said shrugging his shoulders. "But I'm going to make a move and ask her out Friday."

Dan swallowed nervously. "Good for you man, hope it works out."

"What are you doing after practice? Want to get something to eat," Nate asked chewing on his gummy bears and smiling after he closed his locker.

"No, but I have to go to Blair's so we can work on our project," Dan said as he stood up from the wooden bench.

Nate knitted his brows together. "You guys already started on that?"

Dan raised his brows. "We're almost finished."

"I hate you guys," Nate said shaking his head causing Dan to chuckle

**XOXOXOXO**

With each step up the staircase of Blair's penthouse, he felt his heart thump harder and harder. Blair didn't act any different towards him during school. She pretended as though he didn't exist. A part of him regrets developing feelings for her because before, they were friends and would banter out in the open.

When he stepped foot onto the hallway, a trail of Chanel No. 5 had passed through leading his eyes to close.

He reached her door and knocked lightly.

"Come in," he heard through the door.

Opening the door and stepping into Blair's room, he found her looking over herself in the mirror while still wearing her Constance uniform.

Dan cleared his throat and sat on the edge of her bed after dropping his messenger bag. "So I started writing presentation notes on a notecard. I brought extra notecards just in case you wanted to do it as well."

"What's your favorite flavor," Blair asked with her back turned to him as she sat in front of her mirror.

"Um…Vanilla I suppose," Dan said sounding confused

He watched her search through her array of lip glosses before she finally picked one out and glossed it over her lips.

"About last night, weren't you supposed to be mad at me?"

Blair slid off her small ottoman and stood in front of him with her hand on her hip. "Yes, and deservedly so, you've been quite awful." Blair then folded her knees on either side of Dan and positioned herself on his lap with her arms wrapped around his neck. "But a story goes a long way."

"So you liked it?"

A smirk tugged her lips. "It was passable," Blair said indifferently. "Now stop talking." Blair moved in but to her surprise Dan turned his head.

"Nate's going to ask you out on Friday," Dan told her

"So?"

"He gave you that necklace and is clearly head over heels in love with you," Dan reasoned

"Oh please, one which he cannot afford," Blair huffed looking frustrated. "He obviously didn't buy it, I asked him how much it cost and he told me it was 290 dollars which I know is wrong since I go to the Tiffany's store practically every 2 weeks."

Dan rubbed his face in annoyance.

Blair slowly unfolded her knees and wrapped her legs around Dan's waist. "Now, if you aren't going to tell me who bought it, then I can think of something better to consume our time with."

She leaned in and pressed her lips against his and began to suck on his bottom lip while kissed the top. She was an aggressive kisser. Her kisses felt like they had many meanings behind them, like all her feelings and emotions were placed onto her kiss.

Dan pulled away fighting against Blair's persistent lips. "How do you feel about me?"

"Humphrey, you're talking too much," Blair replied

"I need to know Blair, I can't do this without it being real," Dan said. "So again, how do you feel about me?"

Blair pursed her lips and smiled. "I don't hate you."

Dan brushed the strands of her hair away and reached for her cheek. "Well, I really like you," Dan admitted softly, looking into her eyes. "I liked you enough to buy you that necklace from Tiffany's."

"You bought it," Blair's voice cracked

"Yes, because there is no price on your happiness for me," Dan said

He watched her slowly untie her bow tie and toss it on the floor while staying on his eyes. She then began unbuttoning her white blouse, starting with her collar and working her way down in a painstakingly slow pace. He started getting hard at sight of her creamy skin. His mind began to trace off to Nate. Guilt was beginning overwhelming him, he shouldn't be doing this. But then her azure bra popped off and worrying about Nate was thrown out the window at the sight of her bare breasts.

Once Dan's hand slowly reached for her left breast, Blair shut her eyes to his gentle squeeze and took a deep breath through her nose while slightly tilting her chin upwards.

He couldn't believe she was letting him touch her white pristine breasts. He knew how untouchable she was, how it was impossible to be let in. It didn't feel real because she was so special, unlike any other girl in the world.

She took his other hand and placed it on her right breast leading him to control himself from dropping his jaw. He wondered how many other guys got to touch her like this. Her relationship with Nate didn't seem to be the very passionate, they rarely touched each other in public from what he remembered. Of course there was Carter, but that relationship didn't last long and she's still a virgin.

All his thoughts were forgotten when he felt her lips on his. The taste of vanilla caused him to smile against her lips. He heard a moan against his lips when he pinched her nipple. Eventually, he parted his lips to let her tongue in which was strong. It wasn't surprising, if anything, it explained a lot.

Gently sliding his hand down to her panties, he found her them to be soaking. He hated her tights because there wasn't enough bare skin and the extra work it would take just to take them off.

Dan pulled away from her lips and gently led her down to her back. "I don't think putting these in the wash will do you any good," Dan said and tore her panties earning a yelp from Blair.

Lying side to side on the bed, facing each other, he began rubbing her clit as Blair began sucking and biting his neck while grabbing a hold of his hair. He slid his fingers off her clit and inserted a finger into her entrance earning him a light moan. He then added another finger leading Blair to whimper against his neck.

Gently thrusting his fingers in and out of her entrance was causing her to leave her mouth open and her eyes to close as a wave of orgasm was on the breach of hitting her.

Watching her become undone was the most exquisite thing he had ever seen. It was the way her face twisted and her sheets crumpled under her fingers that made it so special. With her chest flushed and her breathing slightly irregular, Blair slid closer to snuggle against his chest leading him to press her closer with his arms.

She seemed serene and in a state of tranquility while millions of questions were running through his head. All he knew was that he didn't want to lose her. He was into deep now.

* * *

**R&R are always appreciated**


	6. Chapter 6

**A/N: I just wanted to remind my readers that this story takes place in the years 2007-2008. Also, you will get Chuck's side of the story of what happened between him and Jenny. **

**Thank you for the reviews and alerts. They really make my day.**

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Typically, the normal American spends the day before Thanksgiving either on a plane or with their families catching up, but that wasn't the case for Dan. Instead, he was in the ballroom of some five star hotel, impeccably dressed wondering if there was any way of getting a hold of some alcohol.

For the past few weeks, he had been sneaking around with Blair. Gossip Girl had spotted them spending time together a few times, but only had them marked as friends which already caused a stir. Queen B spending time with someone from Brooklyn was unfathomable. To the UES, it went against everything Blair Waldorf believed in.

"This is bullshit, we have to watch our parents get loaded while we stay sober and make sure they don't embarrass themselves," Nate said with a crowd of well-dressed adults surrounding them.

"Good thing my dad isn't a drinker," Dan told him.

Nate's eyebrows knitted together. "Where the hell were you last night anyway? Weren't we supposed to catch the Seven O'Clock showing to Superbad last night?"

_Last Night…._

"_Admit it, you liked it," Dan said as him and Blair reached her door_

_Blair raised her brows. "I don't do raunchy Humphrey."_

"_I'm sorry, but I thought Superbad was hilarious. You just don't like to see how much fun life can be outside the UES."_

_Blair rolled her eyes and opened the door to find a candle lit room. He stood there stunned as Blair grinned and pulled him towards the bed. _

"_Are you sure," Dan asked with his hands on her hips and Blair straddling him on his lap._

"_Yes," Blair said softly and leaned her forehead against his. _

"_So you're ready to have the most mind-blowing 2 minutes of your life," Dan teased with a smile_

_Blair giggled. "Humphrey! You're ruining the mood. You're supposed to be sexy right now."_

_Dan flipped her over on the bed with a smirk earning a squeal. _

"I went to watch Superbad with Blair," Dan told Nate as he turned to him

"Dan! What the hell?"

"I know, I'm sorry man," Dan said with his lips on his cola.

"How can you watch that without with me? That movie was made for watching with your buds," Nate reasoned. "I bet Blair didn't even like it."

"Yeah, she didn't," Dan confirmed. "What'd you do last night?"

"I went to Chuck's suite, he was having a party." He followed Nate's eyes over to Blair standing with Serena. "I just don't understand why Blair's wearing that necklace if she doesn't want to be with me. I would understand it if she wore it on occasion, but she has it on every day."

Dan swallowed hard as he felt his throat tighten and shrugged his shoulders. "She's an enigma."

Hiding his relationship from Nate was eating him alive because Nate deserved to know, but he didn't even know how strong Blair's feelings for him were.

Nate and Dan eyes fell to Chuck walking past them with a slight limp.

Nate turned his head back to Dan. "Have you noticed something off about the way Chuck's been walking?"

"I have, maybe you should ask him about it," Dan said with a smirk

"It was weird, Katie was all over him last night, but he pushed her away."

Dan bit back a smile before he took a sip from his cola. "Interesting."

Nate was back to being best friends with Chuck and everything was forgotten as it usually was in the Upper East Side.

Leaving Nate, he saw Blair standing alone holding a drink in a backless black evening gown with a side split exposing her bare leg.

"Waldorf," Dan said

"Humphrey," Blair stated simply lifting her chin high. She turned to face him and her brown eyes fell on his hair. "Your hair."

A crease formed in-between Dan's eyebrows. "What about it."

"It's actually well-kempt," Blair said. A smile began to form on his lips from watching her chew on her lip nervously. "It's nice," Blair admitted softly looking away from him. "It was too short before."

Dan tilted his head to meet her eyes. "If only there was something I could point out, but it's too difficult with someone so flawless," Dan replied

Blair looked down and smiled, brushing her lock of hair behind her ear.

"Nothing is more beautiful than a smile that has struggled through tears," Dan said and watched Blair shut her eyes while taking in his words.

"Mmmmm, Blair, may I say you look amazing tonight," Chuck told Blair stepping in and then noticed her looking a bit off. "Are you alright?"

Blair pursed her lips and smiled. "Yes, I'm fine, just heading towards the girls room," Blair said walking away. His eyes remained on her as she walked through the crowd. She then turned her head and locked eyes with his, giving him an intense gaze before heading out of the ballroom.

"Humphrey, still upset I see," Chuck said

Dan shook his head and looked at him in disbelief. "Why wouldn't I be you fucking gremlin?"

Chuck recoiled slightly to his words. "Dan, you don't understand, it was consensual, I didn't put any pills in her drink. Even Jenny doesn't think she was raped, you're the only one who seems to be strung up on the idea," Chuck stated

"Okay, let's say it was consensual, what you did to her was still fucked up. She's my sister and you're supposed to be my friend."

"Open your eyes Humphrey. You're sister isn't so innocent," Chuck said with his nostrils flaring. "She left me on the rooftop with nothing but a pair of boxers. Do you really think I would let her get away with that?"

He didn't know his sister was the one who started this squabble with Chuck.

"No." Dan looked down at his drink and shook his head. "But she clearly had feelings for you and you hurt her badly."

"Listen, I've made up with Nate, and I'd like to make up with you as well so everything can be back to normal," Chuck told him.

Dan nodded. "Okay."

"So we're good?"

"Yeah, we're whatever man."

**XOXOXOXO**

After Blair left for the bathroom, Dan received a text to meet her at the bar. Heading out of the ballroom and into the marble floored lobby with the bright chandeliers lighting the foyer, he found a group of well-groomed male adults chatting with their alcohol beverages in hand. He walked past them into a dark lit room where he found a cabin like designed bar with a fireplace and dark pinewood walls. There were heads of dead animals and the room was filled with chic men discussing politics and social issues while drinking by the fire place. His eyes scoped the room until he saw Blair seated on a stool with her elbows on the bar, waiting for a drink.

"I guess there some perks to not having your mother attend," Dan said pulling up a stool to sit next to Blair. He wished he wasn't leaving with his father, at least then he would've been able to get drink.

Blair met his eyes and played with her necklace as she bit her enticing lip. "No more compliments?"

His lip curved slightly at the thought of her fishing for compliments. He placed his slender fingers on her warm thigh, causing her breath to hitch, unnoticeable to most, but not him. The effect he had on her should be surprising, but after spending weeks with her, he's becoming accustomed to it. Once he felt her tantalizing fingers move on top of his hand, he leaned closer into her breathing space.

"When you look at me with those dark, alluring eyes, I don't see anyone else. Those golden flecks make me feel like I could swim in them for days," Dan told her softly and then leaned into her ear. "It's just too easy when it's true," Dan whispered.

Her doe eyes stayed on him with her lips quivering. His eyes fell on her lips as his nostrils were becoming consumed with traces of jasmine and cyclamen from her hair. Her eyes were inviting him to meet her lips.

Dan cleared his throat. "So, Thanksgiving's tomorrow," Dan said raising his brows and trying to change the mood.

Blair beamed and it looked as though her eyes were sparkling. "Yes, you'll finally get to meet Daddy."

The Van Der Woodsen's were coming to the Waldorf's for Thanksgiving which he didn't think was a good idea. Having that many people with so much history was never a good idea. It would only lead to meaningless drama.

"What's he like," Dan asked

He watched her smile thinking about the past before her parents divorced, when her life was perfect. There's a hint of shyness in the way she's mulling over how to describe her father. Whenever they were alone, it felt like he was with a different Blair Waldorf. The Queen B side to her was just a wall, or maybe it was real, he didn't know, and that's what made her so alluring. She kept him on his toes. Unlike most of the superficial girls attending Constance, there were layers to her.

"He's soft, loves to spoil me, he cares for me and wants to see me happy," Blair said smiling to herself while playing with her martini.

"He gives you what your mother doesn't," Dan added

Blair turned her head to meet his eyes. "Exactly."

"My mom left for France to discover herself, but the problem was that she totally forgot about us," Dan confessed smiling and shaking his head in disbelief as he looked straight ahead. "I was in the ninth grade when we found out she met someone and wasn't coming back."

"She left your father," Blair asked softly and he felt her grip his hand tighter

"Yeah, and you'll get to meet her tomorrow."

**XOXOXOXO**

It was the day of Thanksgiving and everyone would be attending the Waldorf's. Eleanor even invited the Bass men since they didn't have anywhere else to go. Celebrating Thanksgiving in the Upper East Side was strange, his Thanksgiving's typically consisted of helping his mother and father in the kitchen by helping them cook for the whole day. But at Eleanor's, everyone was in the living room chatting while the kitchen was occupied with a professional cooking dinner.

Sitting on the ottoman of the living room with Blair, he watched Jenny model out her newly bought clothes. Unlike him, his sister was using the perks of his father marrying rich.

"So what do you think," Jenny asked him swirling around

"Wow, you don't look so ugly today," Dan said earning a giggle from Blair and Serena. Jenny gave him a glare for the ages. "I'm sorry, but I'm not really the person to ask."

Jenny breathed out a sigh of annoyance and stomped out of the room leaving him with Blair and Serena. Nate's family was at his Grandfather's and he was left with mostly women.

As the day progressed, he came to the realization Blair's father wasn't coming. He tried to get a read on Blair, but it didn't seem to be affecting her in any way. Eleanor wasn't making the situation any better as she scolded Blair for eating chocolates.

Allison and Lily spent the day verbally sparing with each other. He couldn't believe how envious his mother was of Lily. His mother was displeased they were spending Thanksgiving in the Upper East Side and it led to a dispute between his mother and father. He thought it was ridiculous and his mother had no right. She left them and was pissed they were better off without her.

"Just get the hell out mom," Dan said leading the dining room to fall silent. "I'm so tired of you complaining about how we're going to be spoiled and this world isn't for us when you spent the past year fucking some hippy and pretending you didn't have any kids back home."

"Daniel, what has gotten into you," Allison stated in disbelief

"I'm tired hearing you complain, you're clearly jealous, so please, go back to your bearded boyfriend." He looked over to his stunned father. "I don't know why we're pretending like she's actually a part of this family." He pushed off his chair and left the dining room with his mother speechless.

His mother never came to confront him, she did what she does best, she left without a word.

Later on, after his mother left, and he had received a lecture from his father, he found Blair looking like she was on the verge of tears in the secluded kitchen. He saw her eating out of a box of chocolates and frowning.

"Do you mind if I have one," Dan asked with a smirk

"No, there aren't any left," Blair said sounding slightly irritated with his presence

"What are you talking about? There are two boxes right in front of you." Dan's brows knitted together as he tilted his head. He stepped closer and reached for her arm only to be shaken off. "What's wrong?"

"Leave me alone Humphrey," Blair stated firmly, squaring him a glare.

"Hey." Dan reached for her cheek. "It's me, you can tell me."

Blair pushed him off and grabbed the boxes of chocolates from the kitchen counter. "Don't touch me!"

"Blair," Dan said softly looking worried.

She tried to walk away but Dan grabbed her wrist before she could reach the doorway. Her eyes were watery but her jaw was clenched. "Let go of me," Blair said but he held on. "Go back to the homeless shelter Lily found you in."

He finally let go as the words coerced through his heart. She knew he always felt insecure about where he came from. She finally got what she wanted and he watched her ascend up the staircase with her box of chocolates, leaving him hurt and vulnerable.

_Who the hell eats that many chocolates? _

**XOXOXOXO**

It was getting late and Chuck invited everyone to his suite in the Palace and Nate decided to meet them there as well. He thought he might as well invite Vanessa, since he had to introduce her to his friends at some point.

Blair and Serena went to Chuck's without him while he left to pick Vanessa up in Lily's town car. Vanessa was surprised and displeased to be riding in a town car. She felt this wasn't him and warned him about letting the UES change him. At the moment, he could care less to what Vanessa was telling him. He was pissed and hurt at what happened with Blair earlier and it was ruining his night.

As they entered Chuck's suite, they found Serena dancing by herself near the stereo, while Chuck and Nate were playing pool with drinks in their hand. He looked over to Vanessa and she cocked an eyebrow. Once the door shut, everyone's eyes fell on them. Chuck and Nate looked intrigued by Vanessa's presence while Blair scrunched her face.

"Well well, if it isn't the troll from the west," Blair said with a wicked smile sitting on the leather sofa chair.

"Ignore her, she's just P.M.S-ing today," Dan retorted leading Blair give Dan a glare.

"Hi, I'm Chuck Bass," Chuck stated with a smug grin

Dan glanced over to Vanessa. "Yes, and he's a perv." Dan pointed to Nate. "That's Nate, and you've already met Serena and Blair."

After having a drink, he began playing pool with Nate, Blair and Chuck while the Serena and Vanessa were talking amongst themselves in the living room. For some reason, Blair had a certain dislike for Vanessa and spent her time with them.

"Stop eyeing her Bass," Dan said

Chuck smirked and struck the white ball with his pool stick. "Someone's being protective. I didn't realize you and her had a thing."

"We don't, but she's my best friend and you disgust me," Dan told him

"You should make a move tonight," Nate added

"On Vanessa?" Dan's brows furrowed in confusion. "No way, we're just friends."

"Dan, I haven't seen you with anyone. Aren't you getting a bit lonely there," Nate teased with a smile. "Come on Danny boy, let's see how much game you have."

"Humphrey and game? Please," Blair scoffed rolling her eyes.

Blair was beginning to irritate him. "Okay, I'll do it, but I'm making a move on Serena instead," Dan said meeting Blair's eyes.

"Perfect, I'll take Vanessa," Nate replied with a smile and patted Dan's back. "Be my wingman and I'll be yours."

"And I'm left with Blair," Chuck said staring at Blair causing her to scrunch her nose.

He wasn't planning on doing anything with Serena, but Blair was getting under his skin and he just wanted piss her off. With him sitting in between Blair and Serena, he felt Blair's brown eyes burning through to his soul. It was as though she was pleading with him not to flirt with Serena.

Nate wasn't making much progress himself as Vanessa didn't seem to find his charm appealing, so Chuck thought it might be a good idea to get the Vanessa drunk to loosen her up. Serena came up with the idea of playing I Never.

"I never paid money for sex," Nate said and everyone other than Vanessa looked at Chuck waiting for him to take the shot. Chuck shook his head and drank from his shot glass.

It was his turn so he decided to mess with Chuck. "I never had sex with a transsexual," Dan said and looked at Chuck. Noticing his shoulders slump and hearing him sigh in defeat, Chuck took another shot. "I knew it," Dan yelled with a grin and looked over to Nate. "I told you!"

Apparently Chuck had a wild weekend in Thailand and he found the next night that the prostitute he slept with the previous night had a penis. Chuck's plan of getting Vanessa drunk backfired as everyone got the hint to strategize against Chuck.

**XOXOXOXO**

With a passed out Chuck lying on his sofa, Dan decided to call it a night and Vanessa followed. They reached the hallway and waited for the elevator.

"You were pretty cold to Nate tonight," Dan said with Vanessa flicking through her cellphone

The dark haired brunette looked up. "He was a little forward."

Smile crept up Dan's lips. "What's the problem with that?"

Vanessa sighed and looked down taking a moment to collect herself before she looked back up to meet his eyes. "See, the problem is... I'm hung up somebody else." Vanessa's lips curled into a smile. "He's this cute, curly haired boy, whose words can make a girl float for days."

Dan tilted his head and a crease formed in-between his brows as well as his forehead. "You're serious," Dan inquired with surprise resonating from his voice.

"Yes." He felt her soft moist hands reach for his. "I was such an idiot for not saying it back. It scared me, but when I left, I couldn't stop thinking about you."

"There was a time when I loved you, but two years have passed since then. I had to move on."

"With her, the girl whose nose twists every time I enter the room," Vanessa asked and shook her head in disappointment. "She doesn't want you and never will."

There was hurt resonating from her voice and he could notice a tear threatening to creep out from the corner of her eye. He remained speechless to her sniffing before the elevator finally opened.

Vanessa stepped in and held her hand out before he could join her. "Please, I need to be alone right now." Dan nodded and watched the elevator door close.

He caught a whiff of Chanel No. 5 and turned around to find Blair behind him with her arms crossed in black overcoat looking nervous. Her heel was tapping rapidly against the carpeted floor and it looked as though she was biting her cheeks.

"You look a lot better than you did this afternoon," Dan said as his hands were in shoved his pockets while he twisted and turned with his weight on the heels of his suede boots.

Her small fingers reached and intertwined with his. "She's wrong, I do want you," Blair murmured before placing a soft kiss on his knuckles.

"Then what the hell was that today? I get a fight with my mom but you seemed too busy to care. Then I find you stuffing your face with chocolate while on the verge of tears. So I try to help, and you just degrade me."

"It's just…."

"What," Dan asked softly. He watched her swallow before her eyes shifted back and forth as she was figuring out how to put everything into words. He reached for her cheek and saw a tear roll down her cheek. "You can tell me anything."

"Daddy didn't come to Thanksgiving because my mother lied. She told him I didn't want him there," Blair explained and leaned into his chest leading him to press her closer with his arms. "I'm sorry for saying those things, it's a defense mechanism." Blair sniffed. "I'll work on that."

Eleanor Waldorf had become a mystery to him. She clearly didn't understand the how much she was hurting her daughter.

"No, I'm sorry Blair," Dan said with his chin resting on top of her head. "Why don't we go back to the loft where we'll be alone tonight and talk about it over some tea?"

"I'd like that," Blair muttered softly against his chest.


	7. Chapter 7

**This is the penultimate chapter. Sorry it has taken me so long to update this fic, I just haven't been very satisfied with the way the chapter turned out. I hope to update my other fic, "Brighter as We Fall" soon, maybe within this week to next week. I also have another Dair fic in the works and it will probably be my last story for this specific fandom.**

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She couldn't stop touching him and he couldn't tell her to stop. Dan was only able to stay at the Charity Ball for thirty minutes before sneaking out with Blair.

He sat in her town car with his hand under her dress. She had him straddled and didn't care what the driver was thinking. Forming his two fingers into scissors, he pushed her silk panties aside and slid his fingers into her warm core, causing her to moan very lightly against his lips. He pulled back and tilted his head to stare at her with fascination reeking through his eyes. Her mouth was open and there was a light pleasurable noise mixed in with a heavy breath escaping her lips.

Leaning his lips on to her neck, he decided he was going to leave a mark. It was tiring having to watch all the guys stare at her. He wanted them to know she was taken. He never thought he was the possessive type, but it's different with her. Her running away was always in the back of his mind. He left his thoughts when her arm tightened around his neck and her hand was pulling his hair harder.

_She was close _

He pulled away from her neck and met her eyes. "Not yet darling." Dan then pulled his fingers out of her core and irritation crept up her face. He wanted to frustrate her because he knew it only made her cum harder. Once he placed his fingers in his mouth to taste her, all was fixed as she bit her plump lip.

She began nuzzling her nose against his cheek and he could feel her nostrils inhaling his cologne. "What do I taste like?"

"Unreal... Something dropped straight from heaven." He felt her smile against his cheek and jaw.

She moved to his ear. "I was wet the minute you walked in," Blair whispered before biting his earlobe.

He didn't think his pant's could be any tighter around his member. It was burning to be inside her. Their eyes connected and it looked as though she could read through his pain. He knew he was in trouble once her lips curved into a devilish smile. She dug her nails into his shoulders and began rocking her hips slowly against his hard on. It was becoming too much.

"Blair... I can't...stop," Dan struggled to say

"Tish tish Daniel, you know the rule," Blair replied before leaning close to his ear. "Ladies come first."

The whole ride continued to be a torturous affair until they reached her building. She grabbed his hand and pulled him into the lobby. Stepping into the elevator, he hoisted her up against the wall and rubbed his member against her warmth. She moaned and whimpered while his lips remained on his favorite part of her body, her neck. He didn't know what it was about her neck that he loved. Maybe it was the scent of jasmine or maybe it was the sounds she made in response.

After the elevator door opened, his lips never left hers as he pressed her against the wall of the foyer, then the door frame of the living room, and eventually they fell on the white ottoman of her living room.

With her tights to rolled to her ankles, and him pinning her hands above her head, he thrusts into her slick folds. His forehead was leaning against hers while he gave her deep hard strokes into her core.

They didn't last very long. He felt her clenching around him, with a wave of orgasm approaching. It hit her and she cried with pleasure as her legs trembled around his waist and her face twisted in a way he couldn't have found more beautiful. He continued to thrust with their foreheads meeting until he finally released his warm liquid into her.

**XOXOXOXO**

He's spent, but it was December and he had a craving for some hot chocolate. He pulled up his pants and headed towards the kitchen with Blair following his every step. She's never had hot chocolate and he's never had macaroons, so they both decided to try something new.

"So what do you think," Blair asked after he took a bite out of the macaroon

"Eh," Dan shrugged as they stood in her kitchen.

"I'm not surprised you feel that way, seeing as it's missing the ingredients of pork and cheese." Blair swiped the half bitten macaroon from Dan's hand and placed it back in her box. "Oh well, more for me I suppose."

Without her heels, she was shorter then he expected. He placed his hand behind her lower back, liking the feeling of her dark teal floor length dress.

"Go on, I haven't gotten all night, make your hot chocolate," Blair said crossing her arms and turning to face him.

"Do you even have the ingredients? I need a bar of pure cocoa chocolate," Dan told her

"Yes Humphrey. I was tired of hearing the complaints coming out of your Brooklyn mouth."

Dan tilted his head furrowed his brows. "Ahh...I never complained and I only asked you once if you had any."

Her lips pressed tightly. "Funny how we hear things differently."

Dan's lips curved slightly. "You're mad."

"And you're ugly, but please, continue to state the obvious."

Dan stepped closer and pulled Blair's hips to meet his. "If I was so ugly, then why would you let me do this," Dan asked softly and squeezed her butt cheeks with his hands, earning a gasp from Blair.

"Because I pity you," Blair said softly as he leaned in to where his lips were mere inches away from hers.

He smiled before placing a peck on her lips, then two pecks, and Blair finally pulled him in for a kiss. With is lips not tearing away from hers, he led her to the island in the middle of the kitchen and placed her on the marble top of the island.

Dan pulled away from her persistent lips and smirked. "Now sit and watch while I make you the most glorious hot chocolate."

She presented him a fake sweet smile and said, "I really can't wait."

As Dan began cutting the chocolate off the cutting board, he heard a Gossip Girl alert. He didn't reach for his phone, thinking Blair would tell him anyway, but what he didn't expect was his voice coming out of her phone. He glanced over and found her in a fit of giggles while on the cusp of falling off the island as her eyes were on the phone screen.

"Oh my god! How did Gossip Girl even get this," Blair said laughing

_Fucking Nate_

He's come to the realization Nate videotaped him singing in the shower.

"I mean what are you even singing?"

"Short Skirt Long Jacket by Cake," Dan told her feeling the heat rising on his neck and cheeks.

"Well the lyrics do remind me of a certain someone," Blair replied sliding off the island. Her lips began forming into a pout. "Aww Humphrey, I'm flattered."

Dan rolled his eyes and shook his head. "We're scheming against Nate tomorrow."

"Of course, I'll come up with something tomorrow. No one hurts my baby," Blair reassured him in her baby voice while rubbing his back soothingly with her hand.

Dan sighed tiredly knowing this wasn't going to end anytime soon.

**XOXOXOXO**

It's lunch time and Winter Formal's around the corner. He wanted to take Blair to the dance and let it be known that they were dating.

He spotted Nate, Blair, and Serena sitting in the corner of the lunch room by a small rectangular table. He sat beside Blair and her face looked unaffected with his presence.

"We should do a study group for our midterm in English," Nate said with his eyes shifting between Dan and Blair.

Serena perked up. "Oh, that's such a good idea Natie!"

Dan placed his hand on Blair's thigh and felt her place her hand on top of his. "Sure, why not."

"Of course that sounds good to you," Blair said looking at Serena. "Me and Humphrey do all the work while you and Nate pick our brains out."

"I don't see the problem with that," Nate joked with a smirk leading Blair to roll her eyes. "Dan helps me with school and I help him get laid. It's called friendship."

Blair snorted. "Well you sure haven't held your end of the bargain."

"I wouldn't laugh, Dan here has already been asked by a few girls to the Winter Formal," Nate replied

Blair turned her head to meet his eyes and cocked a brow. "Really? Do share Humphrey."

Dan sighed. "It's nothing really, I haven't been asked by anyone that interests me."

"What about you," Serena asked staring at Blair

Blair tilted her head down and her eyes shifted to her fruit bowl. "No, I haven't been asked by anyone yet."

"We should go together," Nate said raising his brows and looking hopeful. "If you want to I mean."

He waited in anticipation for Blair's response as his heart rate shot up.

Blair looked up and met Nate's eyes, giving him a light smile. "Sure, that'd be great."

His heart sank and he was hit with a wave of disappointment. He moved his hand away from Blair's thigh and got lost in his own thoughts, ignoring the rest of the conversation. She tried to reach for his hand under the table, but he pulled away. It felt like he had been slapped in the face with the realization that this was only a fling. He was her dirty little secret.

He left soon after Nate asked Blair to the Winter Formal, telling them he needed to edit a paper.

The school day passed and it was time for soccer practice. He took out his frustrations on the field. Even giving Nate a dirty sliding tackle, leading the coach to throw him out of practice. He hit the showers, cooled off, and got dressed.

As he left the courtyard, he spotted Blair's town car waiting for him. He rolled his eyes and continued on his way to the bus stop. The town car followed his every step as he continued to walk ahead.

The tinted window of the town car rolled down and he saw Blair sitting in the car with sunglasses on.

"Get in Humphrey," Blair said

"No thanks."

"Dan, someone might spot us, please get in the car."

Dan stopped and looked at Blair incredulously. "You're unbelievable. All you care about is how others perceive you."

Blair glared at him. "You've never been in my shoes so you have no right to judge."

"Do you even want to be with me?"

"Yes, of course I do."

"Then go to the dance with me," Dan said feeling like he was left alone on an island.

Her mouth open and closed a few times as she was having trouble putting her feelings into words.

"I can't," Blair told him softly and looked away

_She doesn't want you, she never will._

_I just think you're setting yourself up to get hurt, you don't belong in their world_

Vanessa's word resonated in his head and it hurts thinking about it. He was too infatuated with Blair to realize Vanessa was right all along.

"Because you're ashamed of me," Dan concluded

"No," Blair protested instantly. "It's about how everyone else will react, not me."

He looked at her in disbelief. "Nate and Serena certainly don't think I'm below them."

"I don't think you're below me," Blair reasoned and her bottom began lip trembling. "You're taking this the wrong way."

"No, I think I understand everything perfectly clear. You don't want me to ruin you're status," Dan replied looking hurt. "God." Dan shook his head. "I am so stupid for falling in love with you."

Her eyes were covered with shades, but her mouth was open in shock. He turned his heels and left for the bus stop, not wanting to listen to what she had to say anymore.

**XOXOXOXO**

It's the night of Winter Formal, and he slides into Chuck's limo with Jenny. Blair and Nate are sitting beside each other while Serena is on the other side. He spent the past week avoiding everyone at school so he wouldn't have to speak to Blair. Just the sight of her made his heart sink.

Standing with his back against the wall in his suit and tie, he stared at Blair dancing with Nate in the darkness. For the whole ride, he didn't look at her once, but that didn't last very long. His jaw was clenching and he could taste the bitterness.

"Are you alright," Serena asked interrupting his thoughts as she was yelling over the music.

He glanced over and saw Serena looking as perfect as ever. "I wish someone would spike the punch."

Serena chuckled. "Same, this dance is lame, but it's should to get more interesting."

Dan's brows knitted together. "What do you mean?"

"Georgina's spiking the punch with some EX," Serena told him with a wicked smile. "Welcome to the Upper East Side Brooklyn."

"Jesus Serena, why do you even hang out with that loose canon," Dan asked as Serena just laughed. "It's not funny you crazy woman. This place is about to go off the wall berserk."

He quickly shoots text to Jenny and Nate not to drink the punch.

"Come on Daniel, we're in our youth. So live a little and enjoy the ride," Serena said with a bright smile. The blonde took his hand and pulled him towards the dance floor. "Let's see what moves you're packing."

Dan couldn't help but smile. Serena's Euphoria was contagious. She really could light the room up and there was something special about that. Dancing with Serena wasn't sexy, if anything, it was silly. They both didn't take themselves seriously and that's what he loved about Serena. He was doing the lawnmower while she was doing the sprinkler. They didn't care what anyone thought about them, all they cared about was living in the moment.

They struggled through the crowd and finally reached the wall of the gymnasium, with sweat glistening on their skin. Once he stepped out of the crowd, his phone vibrated and he received a Gossip Girl alert.

_Good Evening Upper East Siders, _

_I just received a scoop that will cause some major turmoil. The virgin queen and lonely boy have been getting friendly, but has lonely boy been told of his new best friend's involvement with little J's and Chuck's short lived affair. It seems our queen had been a big influence on little J's decision to cozy up with Chuck._

_Welcome to the Upper East Side lonely boy_

_You know you love me._

_xoxo,_

_Gossip Girl_

His brows dipped, leading a crease to form on his forehead as he stared at a open mouthed Blair.

With his jaw clenching, his fingers curled into fists and he had the urge to punch Chuck all over again.

He felt a hand on his shoulder, leading him to pull away from Serena's touch. "Get off me," Dan said grinding his teeth together, trying to maintain his composure.

He headed for the back door exit and into the cold, ignoring all of the eyes that were on him.

"Dan," Blair yelled out. He could hear the clicks of her heels against the cement of the sidewalk. "Please, let me explain."

She sounded desperate so he decided to give her a chance and he still couldn't stand the sight of her freezing to death while chasing him around. He turned around with his face stinging from the cool wind.

"I was mad at you, you didn't come to my birthday party, but I only told Jenny Chuck wasn't lying about his feelings for her," Blair explained.

"Oh fuck off Blair. Bass has been trying to nail my sister since school started so don't bullshit me by telling me it was some lame overreaction," Dan said looking at her in disgust.

"It's the truth," Blair protested instantly. She lets a moment pass before stepping closer. "This is why I didn't want everyone to find out about us. There was no way Jenny would've approved."

"Do you blame her? She trusted you Blair," Dan said looking hurt. "I trusted you," his voice breaks off.

Blair reached for his hand. " Dan," she called softly before he pulled away

"Don't touch me!" Dan began stepping back while facing Blair. She looked as though she was on the cusp of breaking. "Stay the hell away from me."

"I don't think I can. I love you," Blair whispered with a tear trailing down her cheek

He shook his head slightly. "I don't believe you."

"You took my virginity Dan, how you could you think I don't love you," Blair questioned with her voice sounding weak

Dan shrugged before turning around and walking away, leaving her by the back entrance of the school.

**XOXOXOXO**

School became different after the Winter Formal. He was alone, but this was a different type of alone. Everyone in school knew of him now, he existed and was the talk of the halls for weeks. His father continuously probed him on why he was ignoring Serena, but he explained midterms as being the reason.

Sitting at the end of the cafeteria by himself, Nate pulled up a chair to sit in front of him.

"It's been a while," Nate said with a small smile

He raised his eyes from his book. "What do you want?"

"I just want everything to be normal again."

At first, he thought Chuck was the only bad one, but he was wrong, they're all horrible in their own ways.

"You're Serena's future step-brother man, this cold shoulder treatment has got to stop, or else our parents are going to begin getting suspicious," Nate explained

"I don't care."

"Why are you taking your anger out on me and Serena?"

Dan dipped his book and bent his back forward to lean in. "Because you're all the same. You and Serena slept together and were forgiven instantly. in the end, there was no repercussion for your mistake. All you people do is hurt each other and never resolve anything. You guys think your little circle is so great, but it's just bullshit in my eyes."

"Come on man, it's not like that."

"I've been sleeping with Blair for the past month. It's exactly like that." Dan slid off his chair and left a speechless Nate at the small rectangular table.

Before, all he wanted to do was become one of them, he found their lifestyle to be glamorous and appealing, but after taking a step back and looking over how much he had changed because of them, he realized he was better off being an outsider. They were on the path of divorce and drama that could scar them for life.

**XOXOXOXO**

_Knock Knock_

She's knocking on his front door, but he doesn't care. He continues to ignore his father giving him the you're better than this speech. Blair's even won his sister over, but he wasn't surprised, his sister looks up to Blair.

Everyday, for the next two weeks, Blair came by the loft, either knocking on his door, or sliding a letter under the little crease beneath his door. All the letter's ended up in the trash, unopened.

"Maybe you should give the poor girl a break," Rufus said watching Dan stab his dinner while sitting by the counter top. "Christmas is in a few days, it's a good time to be a little generous." Dan ignored his father and continued eating.

"You won't be able to reach him dad, I think he prefers hurting Blair," Jenny pointed out taking a bite out of her ravioli.

Dan turned his head to Jenny. "I'm not trying to hurt her."

"And yet you are. If you cared about her, you would at least listen to what she has to say."

"I already did," Dan said

"Once isn't fair to her. I think it's obvious you're just scared because you know the instant you talk to her again, you'll forgive her," Jenny replied

Dan stared at his plate looking to be in deep thought.

After dinner, once Jenny made him feel guilty, he decided to go see Blair.

Taking a step out of Blair's elevator, he walked into her foyer and noticed how quiet it was. Dorota wasn't around and he had no idea where Eleanor was, which was surprising since Christmas was in a few days. He ascended up the steps of the staircase and found Blair's room to be empty. His eyes fell on an old worn out notebook on her dresser.

He's bit startled at first when he realizes its his notebook. It had all of the short stories and poems he had written about Serena. He lost it over a year ago and had been looking for it since. It must have dropped out of his locker and that's how Blair was able to get a hold of it.

He texted Serena and Nate, inquiring about Blair, and they both texted back saying she was at her penthouse. He then looked over the Gossip Girl spotted map, and it had her last spotted here as well. His eyes then fell on her bathroom door.

Stepping into Blair's bathroom, he was hit with a stench of something rotting. His eyes widened at the sight of Blair passed out and splayed across the floor, by the toilet.

* * *

**I'm a horrible person, I know. Hopefully I'll update the last chapter of this fic soon which will be in Blair's POV.**


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